Organometallic compound and organic light-emitting device including the same

ABSTRACT

An organometallic compound may be represented by one selected from the group of Formulae 5 to 8:

CROSS-REFERENCE TO RELATED APPLICATIONS

This is a divisional application based on pending application Ser. No.13/803,650, filed Mar. 14, 2013, the entire contents of which is herebyincorporated by reference.

The present application claims priority under 35 U.S.C. § 119 to KoreanPatent Application No. 10-2012-0099543, filed on Sep. 7, 2012, in theKorean Intellectual Property Office, and entitled: “OrganometallicCompound and Organic Light Emitting Device Including the Same,” whichhereby incorporated by reference in its entirety.

BACKGROUND OF THE INVENTION

1. Field

Embodiments relate to a compound for organic light-emitting devices, andan organic light-emitting device including the compound.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) may be light emitting devices(e.g., self-emitting devices) and may have advantages such as wideviewing angles, excellent contrast, quick response, high brightness,excellent driving voltage characteristics, and the ability to providemulticolored images.

SUMMARY

Embodiments are directed to an organometallic compound represented byFormula 1:

wherein, in Formula 1: M may be a transition metal; X₁ may be N orC(R₅); R₁ to R₅ each independently may be selected from the group of ahydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₃-C₁₀ heterocycloalkyl group, a substituted orunsubstituted C₃-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₂-C₆₀ heteroaryl group, —N(Q₁)(Q₂),—Si(Q₃)(Q₄)(Q₅), —C(═O)(Q₆), and a binding site with an adjacent ligandvia a single bond or a divalent linking group; two substituents of R₁ toR₅ may be optionally linked together to form one selected from the groupof a substituted or unsubstituted C₄-C₂₀ alicyclic ring, a substitutedor unsubstituted C₂-C₂₀ hetero alicyclic ring, a substituted orunsubstituted C₆-C₂₀ aromatic ring, and a substituted or unsubstitutedC₂-C₂₀ heteroaromatic ring; Q₁ to Q₆ each independently may be selectedfrom the group of a hydrogen atom, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, and asubstituted or unsubstituted C₂-C₆₀ heteroaryl group; n may be aninteger from 1 to 3; L may be a monodentate, bidentate, tridentate, ortetradentate organic ligand; and m may be an integer from 0 to 4.

M may be selected from the group of ruthenium (Ru), rhodium (Rh),palladium (Pd), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir),and platinum (Pt).

X₁ may be C(R₅).

X₁ may be N.

X₁ may be C(R₅); R₁ to R₅ each independently may be one selected fromthe group of a hydrogen atom, a deuterium atom, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a methyl group, an ethyl group, an n-propyl group, an i-propylgroup, an n-butyl group, an i-butyl group, a t-butyl group, a pentylgroup, a hexyl group, a heptyl group, an octyl group, a nonyl group, adecyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxygroup, a pentoxy group, and a substituted group that is substituted withat least one selected from the group of a deuterium atom, a fluorineatom, a hydroxyl group, a cyano group, a nitro group, and an aminogroup; and the substituted group may be selected from the group of asubstituted methyl group, a substituted ethyl group, a substitutedn-propyl group, a substituted i-propyl group, a substituted n-butylgroup, a substituted i-butyl group, a substituted t-butyl group, asubstituted pentyl group, a substituted hexyl group, a substitutedheptyl group, a substituted octyl group, a substituted nonyl group, asubstituted decyl group, a substituted methoxy group, a substitutedethoxy group, a substituted propoxy group, a substituted butoxy group,and a substituted pentoxy group.

X₁ may be N; R₁ to R₄ each independently may be one selected from thegroup of a hydrogen atom, a deuterium atom, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a methyl group, an ethyl group, an n-propyl group, an i-propyl group, ann-butyl group, an i-butyl group, a t-butyl group, a pentyl group, ahexyl group, a heptyl group, an octyl group, a nonyl group, a decylgroup, a methoxy group, an ethoxy group, a propoxy group, a butoxygroup, and pentoxy group, and a substituted group that is substitutedwith at least one selected from the group of a deuterium atom, afluorine atom, a hydroxyl group, a cyano group, a nitro group, and anamino group; and the substituted group may be selected from the group ofa substituted methyl group, a substituted ethyl group, a substitutedn-propyl group, a substituted i-propyl group, a substituted n-butylgroup, a substituted i-butyl group, a substituted t-butyl group, asubstituted pentyl group, a substituted hexyl group, a substitutedheptyl group, a substituted octyl group, a substituted nonyl group, asubstituted decyl group, a substituted methoxy group, a substitutedethoxy group, a substituted propoxy group, a substituted butoxy group,and a substituted pentoxy group.

i) R₂ and R₃ may be linked together so that the organometallic compoundis represented by Formula 1A; ii) X₁ may be C(R₅), and R₄ and R₅ may belinked together so that the organometallic compound is represented byFormula 1B; or iii) R₂ and R₃ may be linked together, X₁ may be C(R₅),and R₄ and R₅ may be linked together so that the organometallic compoundis represented by Formula 1C:

wherein, in Formulae 1A, 1B, and 1C: M, X₁, R₁ to R₅, n, L, and m may beas in Formula 1; and the A ring and the B ring each independently may beselected from the group of a substituted or unsubstituted C₄-C₂₀alicyclic ring, a substituted or unsubstituted C₂-C₂₀ heteroalicyclicring, a substituted or unsubstituted C₆-C₂₀ aromatic ring, and asubstituted or unsubstituted C₂-C₂₀ heteroaromatic ring.

The organometallic compound may be represented by Formula 1A or Formula1C; the A ring may be at least one selected from the group of benzene,pentalene, indene, naphthalene, azulene, heptalene, indacene,acenaphthylene, fluorene, spiro-fluorene, phenalene, phenanthrene,anthracene, fluoranthene, triphenylene, pyrene, chrysene, and asubstituted group that is substituted with at least one selected fromthe group of: a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkyl group substituted with at least onehalogen atom, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₃-C₁₀ heterocycloalkyl group, a C₃-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₂-C₆₀ heteroaryl group, —N(Q₁₁)(Q₁₂), and —Si(Q₁₃)(Q₁₄)(Q₁₅); Q₁₁ toQ₁₅ each independently may be selected from the group of a hydrogenatom, a C₁-C₁₀ alkyl group, a C₆-C₂₀ aryl group, and a C₂-C₂₀ heteroarylgroup; and the substituted group may be selected from the group of asubstituted benzene, a substituted pentalene, a substituted indene, asubstituted naphthalene, a substituted azulene, a substituted heptalene,a substituted indacene, a substituted acenaphthylene, a substitutedfluorene, a substituted spiro-fluorene, a substituted phenalene, asubstituted phenanthrene, a substituted anthracene, a substitutedfluoranthene, a substituted triphenylene, a substituted pyrene, and asubstituted chrysene.

The organometallic compound may be represented by Formula 1B or Formula1C; the B ring may be at least one selected from the group ofcyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane,cyclooctane, cyclopentene, cyclopentadiene, cyclohexadiene,cycloheptadiene, bicyclo-heptane, bicyclo-octane, benzene, pentalene,indene, naphthalene, azulene, heptalene, indacene, acenaphthylene,fluorene, spiro-fluorene, phenalene, phenanthrene, anthracene,fluoranthene, triphenylene, pyrene, chrysene, and a substituted groupthat is substituted with at least one selected from the group of: adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine, a hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkylgroup, a C₁-C₆₀ alkyl group substituted with at least one halogen atom,a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, aC₃-C₁₀ cycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀heteroaryl group, —N(Q₁₁)(Q₁₂), and —Si(Q₁₃)(Q₁₄)(Q₁₅); Q₁₁ to Q₁₅ eachindependently may be selected from the group of a hydrogen atom, aC₁-C₁₀ alkyl group, a C₆-C₂₀ aryl group, and a C₂-C₂₀ heteroaryl group;the substituted group may be selected from the group of a substitutedcyclopropane, a substituted cyclobutane, a substituted cyclopentane, asubstituted cyclohexane, a substituted cycloheptane, a substitutedcyclooctane, a substituted cyclopentene, a substituted cyclopentadiene,a substituted cyclohexadiene, a substituted cycloheptadiene, asubstituted bicyclo-heptane, a substituted bicyclo-octane, a substitutedbenzene, a substituted pentalene, a substituted indene, a substitutednaphthalene, a substituted azulene, a substituted heptalene, asubstituted indacene, a substituted acenaphthylene, a substitutedfluorene, a substituted spiro-fluorene, a substituted phenalene, asubstituted phenanthrene, a substituted anthracene, a substitutedfluoranthene, a substituted triphenylene, a substituted pyrene, and asubstituted chrysene.

The organometallic compound may be represented by one selected from thegroup of Formulae 1A-(1), 1B-(1), 1B-(2), 1B-(3), 1C-(1), 1C-(2),1C-(3), and 1D-(1):

wherein, in Formulae 1A-(1), 1B-(1), 1B-(2), 1B-(3), 1C-(1), 1C-(2),1C-(3), and 1D-(1): R₁ to R₅, R₁₁ to R₁₄, and R₂₁ to R₂₈ eachindependently may be selected from the group of a hydrogen atom, adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine, a hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a substituted C₁-C₂₀ alkyl group, asubstituted C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, ananthryl group, a fluorenyl group, a carbazolyl group, a pyridinyl group,a pyrimidinyl group, a triazinyl group, and a substituted cyclic groupthat is substituted with at least one selected from the group of: adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, and atriazinyl group; the substituted C₁-C₁₀ alkyl group and the substitutedC₁-C₂₀ alkoxy group each may be substituted with at least one selectedfrom the group of a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, and an amino group; the substituted cyclicgroup may be selected from the group of a substituted phenyl group, asubstituted naphthyl group, a substituted anthryl group, a substitutedfluorenyl group, a substituted carbazolyl group, a substituted pyridinylgroup, a substituted pyrimidinyl group, and a substituted triazinylgroup; n may be an integer from 1 to 3; L may be an organic ligand; andm may be an integer from 0 to 4.

m may be 1, 2, 3, or 4; at least one of L_(m) may be represented by oneselected from the group of Formulae 2A to 2F:

wherein, in Formulae 2A to 2F: M₁ may be P or As; X_(11a), X_(11b), X₁₂,X₁₃, X₁₄, X₁₅, X_(16a), X_(16b), X_(16c), X_(16d), X_(16e), X_(16f),X_(16g), X_(17a), X_(17b), X_(17c), and X_(17d) each independently maybe selected from the group of C(R₄₀)_(x), N, O, N(R₃₅), P(R₃₆)(R₃₇), andAs(R₃₈)(R₃₉); R_(33″) and R_(34″) each independently may be selectedfrom the group of a single bond, a substituted or unsubstituted C₁-C₅alkylene group, and a substituted or unsubstituted C₂-C₅ alkenylenegroup; R₃₁, R_(32a), R_(32b), R_(32c), R_(33a), R_(33b), R₃₄, R₃₅, R₃₆,R₃₇, R₃₈, R₃₉, and R₄₀ each independently may be selected from the groupof a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₃-C₁₀ heterocycloalkyl group, a substituted orunsubstituted C₃-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, and a substituted or unsubstitutedC₂-C₆₀ heteroaryl group; the C ring, the D ring, the E ring, the F ring,the G ring, and the H ring each independently may be selected from thegroup of a 5-membered to 20-membered saturated ring, and a 5-membered to20-membered unsaturated ring; x may be an integer from 0 to 2; and * maybe a binding site with M in Formula 1.

R₃₁, R_(32a), R_(32b), R_(32c), R_(33a), R_(33b), R₃₄, R₃₅, R₃₆, R₃₇,R₃₈, and R₃₉ each independently may be selected from the group of ahydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a substituted C₁-C₂₀ alkylgroup, a substituted C₁-C₂₀ alkoxy group, a phenyl group, a naphthylgroup, an anthryl group, a fluorenyl group, a carbazolyl group, apyridinyl group, a pyrimidinyl group, and a triazinyl group, and asubstituted cyclic group that is substituted with at least one selectedfrom the group of: a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group,a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinylgroup, and a triazinyl group; the substituted C₁-C₂₀ alkyl group and thesubstituted C₁-C₂₀ alkoxy group each may be substituted with at leastone selected from the group of a deuterium atom, a halogen atom, ahydroxyl group, a cyano group, a nitro group, and an amino group; andthe substituted cyclic group may be selected from the group of asubstituted phenyl group, a substituted naphthyl group, a substitutedanthryl group, a substituted fluorenyl group, a substituted carbazolylgroup, a substituted pyridinyl group, a substituted pyrimidinyl group,and a substituted triazinyl.

The at least one of L_(m) may be represented by Formula 2C; and X_(11a)and X_(11b) in Formula 2C each independently may be selected from thegroup of 0, P(R₃₆)(R₃₇), and As(R₃₈)(R₃₉).

The at least one of L_(m) may be represented by one selected from thegroup of Formulae 2D, 2E, and 2F; the C ring, the D ring, the E ring,the F ring, the G ring, and the H ring in Formulae 2D, 2E, and 2F eachindependently may be a substituted or unsubstituted benzene, asubstituted or unsubstituted pentalene, a substituted or unsubstitutedindene, a substituted or unsubstituted naphthalene, a substituted orunsubstituted azulene, a substituted or unsubstituted heptalene, asubstituted or unsubstituted indacene, a substituted or unsubstitutedacenaphthylene, a substituted or unsubstituted fluorene, a substitutedor unsubstituted spiro-fluorene, a substituted or unsubstitutedphenalene, a substituted or unsubstituted phenanthrene, a substituted orunsubstituted anthracene, a substituted or unsubstituted fluoranthene, asubstituted or unsubstituted triphenylene, a substituted orunsubstituted pyrene, a substituted or unsubstituted chrysene, asubstituted or unsubstituted pyrrole, a substituted or unsubstitutedimidazole, a substituted or unsubstituted pyrazole, a substituted orunsubstituted isothiazole, a substituted or unsubstituted isoxazole, asubstituted or unsubstituted pyridine, a substituted or unsubstitutedpyrazine, a substituted or unsubstituted pyrimidine, a substituted orunsubstituted pyridazine, a substituted or unsubstituted isoindole, asubstituted or unsubstituted indole, a substituted or unsubstitutedindazole, a substituted or unsubstituted purine, a substituted orunsubstituted isoquinoline, a substituted or unsubstituted quinoline, asubstituted or unsubstituted phthalazine, a substituted or unsubstitutedquinoxaline, a substituted or unsubstituted quinazoline, or asubstituted or unsubstituted cinnoline; when the C ring is substitutedwith at least two substituents, adjacent two of the at least twosubstituents may be optionally linked together to form one selected fromthe group of a substituted or unsubstituted C₄-C₂₀ alicyclic ring, asubstituted or unsubstituted C₂-C₂₀ heteroalicyclic ring, a substitutedor unsubstituted C₆-C₂₀ aromatic ring, and a substituted orunsubstituted C₂-C₂₀ heteroaromatic ring; when the D ring is substitutedwith at least two substituents, adjacent two of the at least twosubstituents may be optionally linked together to form one selected fromthe group of a substituted or unsubstituted C₄-C₂₀ alicyclic ring, asubstituted or unsubstituted C₂-C₂₀ heteroalicyclic ring, a substitutedor unsubstituted C₆-C₂₀ aromatic ring, and a substituted orunsubstituted C₂-C₂₀ heteroaromatic ring; when the E ring is substitutedwith at least two substituents, adjacent two of the at least twosubstituents may be optionally linked together to form one selected fromthe group of a substituted or unsubstituted C₄-C₂₀ alicyclic ring, asubstituted or unsubstituted C₂-C₂₀ heteroalicyclic ring, a substitutedor unsubstituted C₆-C₂₀ aromatic ring, and a substituted orunsubstituted C₂-C₂₀ heteroaromatic ring; when the F ring is substitutedwith at least two substituents, adjacent two of the at least twosubstituents may be optionally linked together to form one selected fromthe group of a substituted or unsubstituted C₄-C₂₀ alicyclic ring, asubstituted or unsubstituted C₂-C₂₀ heteroalicyclic ring, a substitutedor unsubstituted C₆-C₂₀ aromatic ring, and a substituted orunsubstituted C₂-C₂₀ heteroaromatic ring; when the G ring is substitutedwith at least two substituents, adjacent two of the at least twosubstituents may be optionally linked together to form one selected fromthe group of a substituted or unsubstituted C₄-C₂₀ alicyclic ring, asubstituted or unsubstituted C₂-C₂₀ heteroalicyclic ring, a substitutedor unsubstituted C₆-C₂₀ aromatic ring, and a substituted orunsubstituted C₂-C₂₀ heteroaromatic ring; and when the H ring issubstituted with at least two substituents, adjacent two of the at leasttwo substituents may be optionally linked together to form one selectedfrom the group of a substituted or unsubstituted C₄-C₂₀ alicyclic ring,a substituted or unsubstituted C₂-C₂₀ heteroalicyclic ring, asubstituted or unsubstituted C₆-C₂₀ aromatic ring, and a substituted orunsubstituted C₂-C₂₀ heteroaromatic ring.

The organometallic compound may be represented by one selected from thegroup of Formulae 3 and 4:

wherein, in Formulae 3 and 4: M may be a transition metal; X_(1a) may beN or C(R_(5a)); X_(1b) may be N or C(R_(5b)); R_(1a) to R_(5a) andR_(1b) to R_(5b) each independently may be a hydrogen atom, a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenylgroup, a substituted or unsubstituted C₃-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₂-C₆₀ heteroarylgroup, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —C(═O)(Q₆), and a binding site withan adjacent ligand via a single bond or a divalent linking group; twosubstituents of R_(1a) to R_(5a) may be optionally linked together toform one selected from the group of a substituted or unsubstitutedC₄-C₂₀ alicyclic ring, a substituted or unsubstituted C₂-C₂₀ heteroalicyclic ring, a substituted or unsubstituted C₆-C₂₀ aromatic ring, anda substituted or unsubstituted C₂-C₂₀ heteroaromatic ring; twosubstituents of R_(1b) to R_(5b) may be optionally linked together toform one selected from the group of a substituted or unsubstitutedC₄-C₂₀ alicyclic ring, a substituted or unsubstituted C₂-C₂₀ heteroalicyclic ring, a substituted or unsubstituted C₆-C₂₀ aromatic ring, anda substituted or unsubstituted C₂-C₂₀ heteroaromatic ring; Q₁ to Q₆ eachindependently may be a hydrogen atom, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₆-C₆₀ aryl group,and a substituted or unsubstituted C₂-C₆₀ heteroaryl group; L may be anorganic ligand; and m may be 0, 1, or 2.

The organometallic compound may be represented by Formula 3, andR_(1a)=R_(1b), R_(2a)=R_(2b), R_(3a)=R_(3b), R_(4a)=R_(4b),X_(1a)=X_(1b)), M=Pt, and m1=0.

The organometallic compound may be represented by Formula 4; andR_(1a)=R_(1b), R_(2a)=R_(2b), R_(3a)=R_(3b), R_(4a)=R_(4b),X_(1a)=X_(1b), M=Pt, and m1=0.

The organometallic compound may be represented by one selected from thegroup of Formulae 3A-(1), 3A-(2), 3A-(3), 3A-(4), 3A-(5), 3A-(6),3A-(7), 3A-(8), and 3A-(9).

wherein, in Formulae 3A-(1), 3A-(2), 3A-(3), 3A-(4), 3A-(5), 3A-(6),3A-(7), 3A-(8), and 3A-(9): M may be platinum (Pt); and R_(1a) toR_(5a), R_(1b) to R_(5b), R_(11a) to R_(14a), R_(11b) to R_(14b),R_(21a) to R_(28a), and R_(21b) to R_(28b) each independently may beselected from the group of a hydrogen atom, a deuterium atom, a halogenatom, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine, a hydrazone, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₁₀ alkyl group, and a C₁-C₂₀ alkoxygroup, a substituted C₁-C₁₀ alkyl group, a substituted C₁-C₂₀ alkoxygroup, a phenyl group, a naphthyl group, an anthryl group, a fluorenylgroup, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, atriazinyl group, and a substituted cyclic group that is substituted withat least one selected from the group of: a deuterium atom, a halogenatom, a hydroxyl group, a cyano group, a nitro group, an amino group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthylgroup, an anthryl group, a fluorenyl group, a carbazolyl group, apyridinyl group, a pyrimidinyl group, and a triazinyl group; thesubstituted C₁-C₁₀ alkyl group and the substituted C₁-C₂₀ alkoxy groupeach may be substituted with at least one selected from the group of adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, and an amino group; the substituted cyclic group may be selectedfrom the group of a substituted phenyl group, a substituted naphthylgroup, a substituted anthryl group, a substituted fluorenyl group, asubstituted carbazolyl group, a substituted pyridinyl group, asubstituted pyrimidinyl group, and a substituted triazinyl group.

The organometallic compound may be represented by one selected from thegroup of Formulae 3A-(1), 3A-(2), 3A-(4), 3A-(6), 3A-(8), and 3A-(9);and R_(1a)=R_(1b), R_(2a)=R_(2b), R_(3a)=R_(3b), R_(4a)=R_(4b),R_(5a)=R_(5b), R_(11a)=R_(11b), R_(12a)=R_(12b), R_(13a)=R_(13b),R_(14a)=R_(14b), R_(21a)=R_(21b), R_(22a)=R_(22b), R_(23a)=R_(23b),R_(24a)=R_(24b), R_(25a)=R_(25b), R_(26a)=R_(26b), R_(27a)=R_(27b), andR_(28a)=R_(28b).

The organometallic compound may be represented by Formula 4-(a):

wherein, in Formula 4-(a): M may be a transition metal; X_(1a) may be Nor C(R_(5a)); X_(1b) may be N or C(R_(5b)); R₂, to R_(5a) and R_(2b) toR_(5b) each independently may be selected from the group of a hydrogenatom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, a phosphoric acid group or a salt thereof, a substitutedor unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstitutedC₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynylgroup, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substitutedor unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₃-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅),—C(═O)(Q₆), and a binding site with an adjacent ligand via a single bondor a divalent linking group; two substituents of R_(2a) to R_(5a) may beoptionally linked together to form at least one selected from the groupof a substituted or unsubstituted C₄-C₂₀ alicyclic ring, a substitutedor unsubstituted C₂-C₂₀ hetero alicyclic ring, a substituted orunsubstituted C₆-C₂₀ aromatic ring, and a substituted or unsubstitutedC₂-C₂₀ heteroaromatic ring; two substituents of R_(2b) to R_(5b) may beoptionally linked together to form at least one selected from the groupof a substituted or unsubstituted C₄-C₂₀ alicyclic ring, a substitutedor unsubstituted C₂-C₂₀ hetero alicyclic ring, a substituted orunsubstituted C₆-C₂₀ aromatic ring, and a substituted or unsubstitutedC₂-C₂₀ heteroaromatic ring; Q₁ to Q₆ each independently may be selectedfrom the group of a hydrogen atom, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, and asubstituted or unsubstituted C₂-C₆₀ heteroaryl group; L may be anorganic ligand; m1 may be 0, 1, or 2; Y₁ may be a single bond or adivalent linking group including at least one selected from the group of—O—, —S—, —N(Z₁)—, —[C(Z₂)(Z₃)]_(a)—, and —[Si(Z₄)(Z₅)]_(b)—; Z₁ to Z₅each independently may be a hydrogen atom, a deuterium atom, a halogenatom, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine, a hydrazone, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkyl groupsubstituted with at least one halogen atom, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₃-C₁₀ cycloalkenyl group, a C₃-C₁₀ heterocycloalkyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, or a C₂-C₆₀ heteroarylgroup, and a and b are each independently an integer from 1 to 4.

Y₁ may be —N(Z₁)—; Z₁ may be at least one selected from the group of aphenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinylgroup, and a substituted cyclic group that is substituted with at leastone selected from the group of: a deuterium atom, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, a C₁-C₂₀alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, ananthryl group, a fluorenyl group, a carbazolyl group, a pyridinyl group,a pyrimidinyl group, and a triazinyl group; and the substituted cyclicgroup may be selected from the group of a substituted phenyl group, asubstituted naphthyl group, a substituted anthryl group, a substitutedfluorenyl group, a substituted carbazolyl group, a substituted pyridinylgroup, a substituted pyrimidinyl group, and a substituted triazinylgroup.

n may be 3, and m may be 0.

n may be 1, and m may be an integer from 1 to 4.

The organometallic compound may be represented by one selected from thegroup of Formulae 5 to 8:

wherein, in Formulae 5 to 8: M, X₁, R₁ to R₅, and L may be as above inFormula 1; m2 may be 0, 1, or 2; X₁₂ and X_(16d) each independently maybe N or C; X₂₁ may be N or C(R₅₁), X₂₂ may be N or C(R₅₂), X₂₃ may be Nor C(R₅₃), X₂₄ may be N or C(R₅₄), X₂₅ may be N or C(R₅₅), X₂₆ may be Nor C(R₅₆), X₂₇ may be N or C(R₅₇), X₂₈ may be N or C(R₅₈), and X₂₉ maybe N or C(R₅₉); R₄₁, R₄₂, and R₅₁ to R₅₉ each independently may beselected from the group of a hydrogen atom, a deuterium atom, a halogenatom, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine, a hydrazone, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenylgroup, a substituted or unsubstituted C₃-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₂-C₆₀ heteroarylgroup, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and a binding site with anadjacent ligand via a single bond or a divalent linking group; twoadjacent substituents of R₄₁, R₄₂, and R₅₁ to R₅₉ may be optionallylinked together to form one selected from the group of a substituted orunsubstituted C₄-C₂₀ alicyclic ring, a substituted or unsubstitutedC₂-C₂₀ heteroalicyclic ring, a substituted or unsubstituted C₆-C₂₀aromatic ring, and a substituted or unsubstituted C₂-C₂₀ heteroaromaticring; and Q₁₁ to Q₁₅ each independently may be selected from the groupof a hydrogen atom, a C₁-C₁₀ alkyl group, a C₆-C₂₀ aryl group, and aC₂-C₂₀ heteroaryl group.

The organometallic compound may be represented by one selected from thegroup of Formulae 5-(1), 5-(2), 5-(3), and 5-(4):

wherein, in Formulae 5-(1) to 5-(4): M, X₁, R₁ to R₅, and L may be as inFormula 1; m2 may be 0, 1, or 2; X₂₁ may be N or C(R₅₁), X₂₂ may be N orC(R₅₂), X₂₃ may be N or C(R₅₃), X₂₄ may be N or C(R₅₄), X₂₅ may be N orC(R₅₅), and X₂₆ may be N or C(R₅₆); and R₄₁, R₅₁ to R₅₆, R₆₁ to R₆₈, andR₇₁ to R₇₄ each independently may be selected from the group of ahydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a substituted C₁-C₂₀ alkylgroup, a substituted C₁-C₂₀ alkoxy group, a phenyl group, a naphthylgroup, an anthryl group, a fluorenyl group, a carbazolyl group, apyridinyl group, a pyrimidinyl group, a triazinyl group, and asubstituted cyclic group that is substituted with at least one selectedfrom the group of: a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group,a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinylgroup, and a triazinyl group; the substituted C₁-C₂₀ alkyl group and thesubstituted C₁-C₂₀ alkoxy group each may be substituted with at leastone selected from the group of a deuterium atom, a halogen atom, ahydroxyl group, a cyano group, a nitro group, and an amino group; andthe substituted cyclic group may be selected from the group of asubstituted phenyl group, a substituted naphthyl group, a substitutedanthryl group, a substituted fluorenyl group, a substituted carbazolylgroup, a substituted pyridinyl group, a substituted pyrimidinyl group,and a substituted triazinyl group.

The organometallic compound may be represented by one selected from thegroup of Formulae 5-(a), 6-(a), and 7-(a):

wherein, in Formulae 5-(a), 6-(a), and 7-(a): M, X₁, R₂ to R₅, and L maybe as in Formula 1; m2 may be 0, 1, or 2; X₁₂ may be C or N; X₂₁ may beN or C(R₅₁), X₂₂ may be N or C(R₅₂), X₂₃ may be N or C(R₅₃), X₂₄ may beN or C(R₅₄), X₂₅ may be N or C(R₅₅), X₂₆ may be N or C(R₅₆), and X₂₇ maybe N or C(R₅₇); R₄₁ and R₅₁ to R₅₇ each independently may be selectedfrom the group of a hydrogen atom, a deuterium atom, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkyl group substituted with atleast one fluorine atom, a C₁-C₂₀ alkoxy group, a phenyl group, anaphthyl group, and an anthryl group;

Y₂ may be a single bond or a divalent linking group including at leastone selected from the group of —O—, —S—, —N(Z₁₁)—, —[C(Z₁₂)(Z₁₃)]_(c)—,and —[Si(Z₁₄)(Z₁₅)]_(d)—;

Z₁₁ to Z₁₅ each independently may be selected from the group of ahydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,C₁-C₆₀ alkyl group, a C₁-C₆₀ alkyl group substituted with at least onehalogen atom, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₃-C₁₀ heterocycloalkyl group, a C₃-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, or a C₂-C₆₀ heteroaryl group; and c and d eachindependently may be an integer from 1 to 4.

The organometallic compound may be one selected from the group ofcompounds 1 to 68:

wherein, in compounds 60-62, Ph may be a phenyl group and Me may be amethyl group.

Embodiments are also directed to an organic light-emitting device,including: a substrate; a first electrode; a second electrode oppositethe first electrode; and an organic layer between the first electrodeand the second electrode, the organic layer including the organometalliccompound.

The organic layer may include at least one selected from the group of ahole injection layer, a hole transport layer, a functional layer havingboth hole injection and hole transport capabilities, a buffer layer, anelectron blocking layer, an emission layer, a hole blocking layer, anelectron transport layer, an electron injection layer, and a functionallayer having both electron injection and electron transportcapabilities.

The organic layer may include an emission layer; the organometalliccompound may be in the emission layer; and light may be emitted from theemission layer based on a phosphorescence mechanism.

The organometallic compound in the emission layer may serve as a dopant;and the emission layer may include a carbazole-based compound as a host.

The carbazole-based compound may be represented by Formula 10:

wherein, in Formula 10: Ar₁ may be selected from the group of asubstituted or unsubstituted C₁-C₆₀ alkylene group, a substituted orunsubstituted C₂-C₆₀ alkenylene group, —C(═O)—, —N(R₁₀₀)—, a substitutedor unsubstituted C₆-C₆₀ arylene group, and a substituted orunsubstituted C₂-C₆₀ heteroarylene group; R₁₀₀ may be selected from thegroup of a substituted or unsubstituted C₆-C₆₀ aryl group, and asubstituted or unsubstituted C₂-C₆₀ heteroaryl group; p may be aninteger from 0 to 10; R₉₁ to R₉₆ each independently may be selected fromthe group of a hydrogen atom, a deuterium atom, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₃-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, and a substituted or unsubstituted C₂-C₆₀heteroaryl group;

two adjacent substituents of R₉₁ to R₉₆ optionally may be linkedtogether to form one selected from the group of a substituted orunsubstituted C₄-C₂₀ alicyclic group, a substituted or unsubstitutedC₂-C₂₀ heteroalicyclic group, a substituted or unsubstituted C₆-C₂₀aromatic ring, and a substituted or unsubstituted C₂-C₂₀ heteroaromaticring; and

q, r, s, t, u, and v each independently may be an integer from 1 to 4.

The carbazole-based compound may be one selected from the group ofcompounds H1 to H30:

The organic layer may include at least one selected from the group of ahole injection layer, a hole transport layer, and a functional layerhaving both hole injection and hole transport capabilities; and the atleast one of the hole injection layer, the hole transport layer, and thefunctional layer having both hole injection and hole transportcapabilities may include a charge-generating material.

The organic layer may include an electron transport layer, and theelectron transport layer may include a metal-containing material.

BRIEF DESCRIPTION OF THE DRAWING

Features will become apparent to those of ordinary skill in the art bydescribing in detail exemplary embodiments with reference to theattached drawing in which the FIGURE schematically illustrates thestructure of an organic light-emitting device according to anembodiment.

DETAILED DESCRIPTION

Example embodiments will now be described more fully hereinafter withreference to the accompanying drawing; however, they may be embodied indifferent forms and should not be construed as limited to theembodiments set forth herein. Rather, these embodiments are provided sothat this disclosure will be thorough and complete, and will fullyconvey exemplary implementations to those skilled in the art.

In the drawing FIGURES, the dimensions of layers and regions may beexaggerated for clarity of illustration. It will also be understood thatwhen a layer is referred to as being “between” two layers, it can be theonly layer between the two layers, or one or more intervening layers mayalso be present. Like reference numerals refer to like elementsthroughout.

As used herein, the term “and/or” includes any and all combinations ofone or more of the associated listed items. Expressions such as “atleast one of,” and “selected from the group of,” when preceding a listof elements, modify the entire list of elements and do not modify theindividual elements of the list.

According to an embodiment, there is provided an organometallic compoundrepresented by Formula 1:

In Formula 1 above, M may be a transition metal.

For example, M may be a Group VI metal, a Group VII metal, a Group VIIImetal, a Group IX metal, or a Group X metal, a Group XI metal, or thelike. In an embodiment, M in Formula 1 may be ruthenium (Ru), rhodium(Rh), palladium (Pd), tungsten (W), rhenium (Re), osmium (Os), iridium(Ir), platinum (Pt), and the like.

In Formula 1, X₁ may be N or C(R₅).

In Formula 1, R₁ to R₅ each independently may be a hydrogen atom, adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine, a hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₃-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅),—C(═O)(Q₆) (where Q₁ to Q₆ each independently may be a hydrogen atom, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, or a substituted or unsubstitutedC₂-C₆₀ heteroaryl group), or a binding site with an adjacent ligand viaa single bond or a divalent linking group.

In Formula 1, R₁ to R₅ each independently may be one selected from thegroup of:

a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₃-C₁₀ heterocycloalkyl group, a C₃-C₁₀ heterocycloalkenylgroup, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthiogroup, and a C₂-C₆₀ heteroaryl group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₃-C₁₀ heterocycloalkyl group, a C₃-C₁₀ heterocycloalkenylgroup, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthiogroup, and a C₂-C₆₀ heteroaryl group that may be substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₁-C₆₀ alkyl group substituted with at least one halogenatom, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxygroup, a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀heteroaryl group, —N(Q₁₁)(Q₁₂), and —Si(Q₁₃)(Q₁₄)(Q₁₅) (where Q₁₁ to Q₁₅are each independently a hydrogen atom, a C₁-C₁₀ alkyl group, a C₆-C₂₀aryl group, or a C₂-C₂₀ heteroaryl group);

—N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —C(═O)(Q₆) (where Q₁ to Q₆ eachindependently may be a hydrogen atom, a C₁-C₆₀ alkyl group, a C₆-C₆₀aryl group, or a C₂-C₆₀ heteroaryl group); and

a binding site with an adjacent ligand via a single bond or a divalentlinking group.

In an embodiment, in Formula 1, R₁ to R₅ each independently may be, forexample, one selected from the group of:

a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof;

a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopropyl group, acyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclopentenyl group, a cyclohexenyl group, a cyclopentadienylgroup, a cyclohexadienyl group, a phenyl group, a naphthyl group, ananthryl group, a fluorenyl group, a chrysenyl group, a pyrenyl group, aphenanthrenyl group, a pyrrolyl group, a pyridinyl group, a pyrimidinylgroup, a pyrazinyl group, a triazinyl group, a carbazolyl group, anindolyl group, a benzoimidazolyl group, a quinolinyl group, anisoquinolinyl group;

a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopropyl group, acyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclopentenyl group, a cyclohexenyl group, a cyclopentadienylgroup, a cyclohexadienyl group, a phenyl group, a naphthyl group, ananthryl group, a fluorenyl group, a chrysenyl group, a pyrenyl group, aphenanthrenyl group, a pyrrolyl group, a pyridinyl group, a pyrimidinylgroup, a pyrazinyl group, a triazinyl group, a carbazolyl group, anindolyl group, a benzoimidazolyl group, a quinolinyl group, and anisoquinolinyl group that may be substituted with at least one of adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine, a hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, ananthryl group, a dimethyl-fluorenyl group, and a phenyl-carbazolylgroup;

—N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —C(═O)(Q₆) (where Q₁ to Q₆ are eachindependently a hydrogen atom, a C₁-C₂₀ alkyl group, a phenyl group, anaphthyl group, or an anthryl group); and

a binding site with an adjacent ligand via a single bond or a divalentlinking group.

In an embodiment, X₁ in Formula 1 may be C(R₅); and R₁ to R₅ eachindependently may be one of, e.g., a hydrogen atom, a deuterium atom, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine, a hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof; a methyl group, an ethyl group, an n-propylgroup, an i-propyl group, an n-butyl group, an i-butyl group, a t-butylgroup, a pentyl group, a hexyl group, a heptyl group, an octyl group, anonyl group, a decyl group, a methoxy group, an ethoxy group, a propoxygroup, a butoxy group, and pentoxy group; and a methyl group, an ethylgroup, an n-propyl group, an i-propyl group, an n-butyl group, ani-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptylgroup, an octyl group, a nonyl group, a decyl group, a methoxy group, anethoxy group, a propoxy group, a butoxy group, and a pentoxy group thatmay be substituted with at least one of a deuterium atom, —F, a hydroxylgroup, a cyano group, a nitro group, and an amino group.

In an embodiment, X₁ in Formula 1 may be N; and R₁ to R₄ eachindependently may be one of a hydrogen atom, a deuterium atom, a halogenatom, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine, a hydrazone, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof; a methyl group, an ethyl group, an n-propylgroup, an i-propyl group, an n-butyl group, an i-butyl group, a t-butylgroup, a pentyl group, a hexyl group, a heptyl group, an octyl group, anonyl group, a decyl group, a methoxy group, an ethoxy group, a propoxygroup, a butoxy group, and pentoxy group; and a methyl group, an ethylgroup, an n-propyl group, an i-propyl group, an n-butyl group, ani-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptylgroup, an octyl group, a nonyl group, a decyl group, a methoxy group, anethoxy group, a propoxy group, a butoxy group, and a pentoxy group thatmay be substituted with at least one of a deuterium atom, —F, a hydroxylgroup, a cyano group, a nitro group, and an amino group.

In an embodiment, in Formula 1, X₁ may be C(R₅); and R₁ to R₅ eachindependently may be a hydrogen atom, a methyl group, an ethyl group, ann-propyl group, a i-propyl group, an n-butyl group, an i-butyl group, at-butyl group, a methoxy group, an ethoxy group, a propoxy group, abutoxy group, a pentoxyl group, or —CF₃. In some other embodiments, inFormula 1, X₁ may be N; and R₁ to R₄ each independently may be ahydrogen atom, a methyl group, an ethyl group, an n-propyl group, ai-propyl group, an n-butyl group, an i-butyl group, a t-butyl group, amethoxy group, an ethoxy group, a propoxy group, a butoxy group, apentoxyl group, or —CF₃.

In Formula 1, two substituents of R₁ to R₅ may be optionally linkedtogether to form a substituted or unsubstituted C₄-C₂₀ alicyclic ring, asubstituted or unsubstituted C₂-C₂₀ heteroalicyclic ring, a substitutedor unsubstituted C₆-C₂₀ aromatic ring, or a substituted or unsubstitutedC₂-C₂₀ heteroaromatic ring.

In an embodiment, i) R₂ and R₃ may be linked together so that theorganometallic compound may be represented by Formula 1A below; ii) X₁may be C(R₅), and R₅ and R₄ may be linked together so that theorganometallic compound may be represented by Formula 1B below; or iii)R₂ and R₃ may be linked together, X₁ may be C(R₅), and R₅ and R₄ may belinked together so that the organometallic compound may be representedby Formula 1C below:

In Formulae 1A, 1B, and 1C, M, X₁, and R₁ to R₅ may be the same as setforth above, and n, L, and m may be as set forth below.

In Formulae 1A, 1B, and 1C above, the A ring and the B ring eachindependently may be a substituted or unsubstituted C₄-C₂₀ alicyclicring, a substituted or unsubstituted C₂-C₂₀ heteroalicyclic ring, asubstituted or unsubstituted C₆-C₂₀ aromatic ring, or a substituted orunsubstituted C₂-C₂₀ heteroaromatic ring.

For example, in Formulae 1A and 1C, the A ring may be at least one ofbenzene, pentalene, indene, naphthalene, azulene, heptalene, indacene,acenaphthylene, fluorene, spiro-fluorene, phenalene, phenanthrene,anthracene, fluoranthene, triphenylene, pyrene, and chrysene; andbenzene, pentalene, indene, naphthalene, azulene, heptalene, indacene,acenaphthylene, fluorene, spiro-fluorene, phenalene, phenanthrene,anthracene, fluoranthene, triphenylene, pyrene, and chrysene that may besubstituted with at least one of a deuterium atom, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkyl group substituted with atleast one halogen atom, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₃-C₁₀ heterocycloalkyl group, a C₃-C₁₀ heterocycloalkenylgroup, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthiogroup, a C₂-C₆₀ heteroaryl group, —N(Q₁₁)(Q₁₂), and —Si(Q₁₃)(Q₁₄)(Q₁₅)(where Q₁₁ to Q₁₅ are each independently a hydrogen atom, a C1-C10 alkylgroup, a C₆-C₂O aryl group or a C₂-C₂O heteroaryl group).

For example, in Formulae 1B and 1C, the B ring may be at least one of,e.g., cyclopropane, cyclobutane, cyclopentane, cyclohexane,cycloheptane, cyclooctane, cyclopentene, cyclopentadiene,cyclohexadiene, cycloheptadiene, bicyclo-heptane, bicyclo-octane,benzene, pentalene, indene, naphthalene, azulene, heptalene, indacene,acenaphthylene, fluorene, spiro-fluorene, phenalene, phenanthrene,anthracene, fluoranthene, triphenylene, pyrene, and chrysene; andcyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane,cyclooctane, cyclopentene, cyclopentadiene, cyclohexadiene,cycloheptadiene, bicyclo-heptane, bicyclo-octane, benzene, pentalene,indene, naphthalene, azulene, heptalene, indacene, acenaphthylene,fluorene, spiro-fluorene, phenalene, phenanthrene, anthracene,fluoranthene, triphenylene, pyrene, and chrysene that are substitutedwith at least one of a deuterium atom, a halogen atom, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkyl group substituted with at least onehalogen atom, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₃-C₁₀ heterocycloalkyl group, a C₃-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₂-C₆₀ heteroaryl group, —N(Q₁₁)(Q₁₂), and —Si(Q₁₃)(Q₁₄)(Q₁₅) (where Q₁₁to Q₁₅ each independently may be a hydrogen atom, a C₁-C₁₀ alkyl group,a C₆-C₂₀ aryl group, or a C₂-C₂₀ heteroaryl group).

In an embodiment, the organometallic compound may be represented byFormula 1A-(1), 1B-(1), 1B-(2), 1B-(3), 1C-(1), 1C-(2), 1C-(3), or1D-(1) below:

In Formulae 1A-(1), 1B-(1), 1B-(2), 1B-(3), 1C-(1), 1C-(2), 1C-(3), and1D-(1), M, and R₁ to R₅ may be the same as set forth above; n, L and mmay be the same as set forth below; and R₁₁ to R₁₄, and R₂₁ to R₂₈ maybe the same as R₁ to R₅ set forth above.

For example, in Formulae 1A-(1), 1B-(1), 1B-(2), 1B-(3), 1C-(1), 1C-(2),1C-(3), and 1D-(1) above, M may be a transition metal (for example,osmium (Os), iridium (Ir), or platinum (Pt)); R₁ to R₅, R₁₁ to R₁₄, andR₂₁ to R₂₈ each independently may be a hydrogen atom, a deuterium atom,a halogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine, a hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxygroup; a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group that aresubstituted with at least one of a deuterium atom, a halogen atom, ahydroxyl group, a cyano group, a nitro group, and an amino group; aphenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, and atriazinyl group; and a phenyl group, a naphthyl group, an anthryl group,a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinylgroup, and a triazinyl group that are substituted with at least one of adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, and atriazinyl group; n may be an integer from 1 to 3; L may be an organicligand; and m may be an integer from 0 to 4.

In Formula 1 above, n may be an integer from 1 to 3. That is, Formula 1above may include one, two, or three ligands represented by Formula 1′:

In Formula 1′, * indicates a binding site with M in Formula 1.

Accordingly, the organometallic compound may include the ligandrepresented by Formula 1′.

If n is 2 or greater, at least two ligands represented by Formula 1′ maybe the same or different.

In Formula 1, L may be an organic ligand, and m may indicate the numberof L's, and may be an integer from 0 to 4. L may be a monodentateligand, bidentate ligand, a tridentate ligand, or a tetradentate ligand.When m is 0, the organometallic compound may include only the ligandrepresented by Formula 1′. If m is 2 or greater, at least two L may bethe same or different.

L may be a suitable organic ligand, e.g., a ligand that does notundesirably change chemical and physical characteristics of theorganometallic compound.

For example, L in Formula 1 may include at least one of the ligandsrepresented by Formulae 2A to 2F below.

In Formula 2B, M₁ may be P or As.

In Formulae 2A to 2F, X_(11a), X_(11b), X₁₂, X₁₃, X₁₄, X₁₅, X_(16a),X_(16b), X_(16c), X_(16d), X_(16e), X_(16f), X_(16g), X_(17a), X_(17b),X_(17c) and X_(17d) each independently may be C, N, O, N(R₃₅),P(R₃₆)(R₃₇), or As(R₃₈)(R₃₉); R_(33″) and R_(34″) each independently maybe a single bond, a substituted or unsubstituted C₁-C₅ alkylene group(for example, methylene, ethylene, or the like), or a substituted orunsubstituted C₂-C₅ alkenylene group (for example, ethenylene or thelike); R₃₁, R_(32a), R_(32b), R_(32c), R_(33a), R_(33b), R₃₄, R₃₅, R₃₆,R₃₇, R₃₈, and R₃₉ each independently may be a hydrogen atom, a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenylgroup, a substituted or unsubstituted C₃-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, or a substituted orunsubstituted C₂-C₆₀ heteroaryl group; the C ring, the D ring, the Ering, the F ring, the G ring, and the H ring each independently may be a5-membered to 20-membered saturated ring, or a 5-membered or 20-memberedunsaturated ring; and * may indicate a binding site with M in Formula 1.

In Formulae 2A to 2F, R₃₁, R_(32a), R_(32b), R_(32c), R_(33a), R_(33b),R₃₄, R₃₅, R₃₆, R₃₇, R₃₈, and R₃₉ each independently may be one of ahydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl groupand a C₁-C₂₀ alkoxy group that are substituted with at least one of adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, and an amino group; a phenyl group, a naphthyl group, an anthrylgroup, a fluorenyl group, a carbazolyl group, a pyridinyl group, apyrimidinyl group, and a triazinyl group; and a phenyl group, a naphthylgroup, an anthryl group, a fluorenyl group, a carbazolyl group, apyridinyl group, a pyrimidinyl group, and a triazinyl group that aresubstituted with at least one of a deuterium atom, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, ananthryl group, a fluorenyl group, a carbazolyl group, a pyridinyl group,a pyrimidinyl group, and a triazinyl group.

For example, if m is 1 or greater in Formula 1 above, L may include aligand represented by Formula 2C above, wherein X_(11a) and X_(11b) inFormula 2C each independently may be, e.g., O, P(R₃₆)(R₃₇), orAs(R₃₈)(R₃₉).

In some other embodiments, if m is 1 or greater in Formula 1 above, Lmay include at least one of the ligands represented by Formulae 2D, 2E,and 2F, wherein the C ring, the D ring, the E ring, the F ring, the Gring, and the H ring in Formulae 2D, 2E, and 2F each independently maybe a substituted or unsubstituted benzene, a substituted orunsubstituted pentalene, a substituted or unsubstituted indene, asubstituted or unsubstituted naphthalene, a substituted or unsubstitutedazulene, a substituted or unsubstituted heptalene, a substituted orunsubstituted indacene, a substituted or unsubstituted acenaphthylene, asubstituted or unsubstituted fluorene, a substituted or unsubstitutedspiro-fluorene, a substituted or unsubstituted phenalene, a substitutedor unsubstituted phenanthrene, a substituted or unsubstitutedanthracene, a substituted or unsubstituted fluoranthene, a substitutedor unsubstituted triphenylene, a substituted or unsubstituted pyrene, asubstituted or unsubstituted chrysene, a substituted or unsubstitutedpyrrole, a substituted or unsubstituted imidazole, a substituted orunsubstituted pyrazole, a substituted or unsubstituted isothiazole, asubstituted or unsubstituted isoxazole, a substituted or unsubstitutedpyridine, a substituted or unsubstituted pyrazine, a substituted orunsubstituted pyrimidine, a substituted or unsubstituted pyridazine, asubstituted or unsubstituted isoindole, a substituted or unsubstitutedindole, a substituted or unsubstituted indazole, a substituted orunsubstituted purine, a substituted or unsubstituted isoquinoline, asubstituted or unsubstituted quinoline, a substituted or unsubstitutedphthalazine, a substituted or unsubstituted quinoxaline, a substitutedor unsubstituted quinazoline, or a substituted or unsubstitutedcinnoline.

In this regard, i) when the C ring includes at least two substituents(i.e., is substituted with at least two substituents), adjacent two ofthe at least two substituents may be optionally linked together to forma substituted or unsubstituted C₄-C₂₀ alicyclic ring, a substituted orunsubstituted C₂-C₂₀ heteroalicyclic ring, a substituted orunsubstituted C₆-C₂₀ aromatic ring, or a substituted or unsubstitutedC₂-C₂₀ heteroaromatic ring; ii) when the D ring includes at least twosubstituents (i.e., is substituted with at least two substituents),adjacent two of the at least two substituents my be optionally linkedtogether to form a substituted or unsubstituted C₄-C₂₀ alicyclic ring, asubstituted or unsubstituted C₂-C₂₀ heteroalicyclic ring, a substitutedor unsubstituted C₆-C₂₀ aromatic ring, or a substituted or unsubstitutedC₂-C₂₀ heteroaromatic ring; iii) when the E ring includes at least twosubstituents (i.e., is substituted with at least two substituents),adjacent two of the at least two substituents may be optionally linkedtogether to form a substituted or unsubstituted C₄-C₂₀ alicyclic ring, asubstituted or unsubstituted C₂-C₂₀ heteroalicyclic ring, a substitutedor unsubstituted C₆-C₂₀ aromatic ring, or a substituted or unsubstitutedC₂-C₂₀ heteroaromatic ring; iv) when the F ring includes at least twosubstituents (i.e., is substituted with at least two substituents),adjacent two of the at least two substituents may be optionally linkedtogether to form a substituted or unsubstituted C₄-C₂₀ alicyclic ring, asubstituted or unsubstituted C₂-C₂₀ heteroalicyclic ring, a substitutedor unsubstituted C₆-C₂₀ aromatic ring, or a substituted or unsubstitutedC₂-C₂₀ heteroaromatic ring; v) when the G ring includes at least twosubstituents (i.e., is substituted with at least two substituents),adjacent two of the at least two substituents may be optionally linkedtogether to form a substituted or unsubstituted C₄-C₂₀ alicyclic ring, asubstituted or unsubstituted C₂-C₂₀ heteroalicyclic ring, a substitutedor unsubstituted C₆-C₂₀ aromatic ring, or a substituted or unsubstitutedC₂-C₂₀ heteroaromatic ring; vi) when the H ring includes at least twosubstituents (i.e., is substituted with at least two substituents),adjacent two of the at least two substituents may be optionally linkedtogether to form a substituted or unsubstituted C₄-C₂₀ alicyclic ring, asubstituted or unsubstituted C₂-C₂₀ heteroalicyclic ring, a substitutedor unsubstituted C₆-C₂₀ aromatic ring, or a substituted or unsubstitutedC₂-C₂₀ heteroaromatic ring;

The above description of the B ring (in Formulae 1B and 1C) may be usedto describe “the substituted or unsubstituted C₄-C₂₀ alicyclic ring, thesubstituted or unsubstituted C₂-C₂₀ heteroalicyclic ring, thesubstituted or unsubstituted C₆-C₂₀ aromatic ring, or the substituted orunsubstituted C₂-C₂₀ heteroaromatic ring,” set forth above.

In an embodiment, if m is 1 or greater in Formula 1 above, L may includeat least one of the ligands represented by, e.g., Formulae 2A(1), 2B(1),2C(1), and 2C(2):

In Formulae 2A(1), 2B(1), 2C(1), and 2C(2), R_(32a), R_(32b), R_(32c),R_(33a), R_(33b), R₃₆, and R₃₇ each independently may be as set forthabove.

In Formula 1, n may be 2. Thus, the organometallic compound may berepresented by Formula 3 or 4 below.

In Formulae 3 and 4, M and L may be as set forth above, and m1 may be 0,1, or 2.

In Formulae 3 and 4, X_(1a) may be N or C(R_(5a)); X_(1b) may be N orC(R_(5b)); and the above-description of R₁ may be used to describeR_(1a) to R_(5a), and R_(1b) to R_(5b).

In an embodiment, the organometallic compound may be represented byFormula 3, wherein R_(1a)=R_(1b), R_(2a)=R_(2b), R_(3a)=R_(3b),R_(4a)=R_(4b), X_(1a)=X_(1b), M=Pt, and m1=0, and may have a transstructure.

In an embodiment, the organometallic compound may be represented byFormula 4, wherein R_(1a)=R_(1b), R_(2a)=R_(2b), R_(3a)=R_(3b),R_(4a)=R_(4B), X_(1a)=X_(1b), M=Pt, and m1=0, and may have a cisstructure.

In an embodiment, the organometallic compound may be represented byFormula 3A-(1), 3A-(2), 3A-(3), 3A-(4), 3A-(5), 3A-(6), 3A-(7), 3A-(8),or 3A-(9) below.

In Formulae 3A-(1), 3A-(2), 3A-(3), 3A-(4), 3A-(5), 3A-(6), 3A-(7),3A-(8), and 3A-(9), M may be platinum (Pt); and R_(1a) to R_(5a), R_(1b)to R_(5b), R_(11a) to R_(14a), R_(11b) to R_(14b), R_(21a) to R_(28a),and R_(21b) to R_(28b) each independently may be one of a hydrogen atom,a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine, a hydrazone,a carboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkylgroup, and a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group and a C₁-C₁₀alkoxy group that are substituted with at least one of a deuterium atom,a halogen atom, a hydroxyl group, a cyano group, a nitro group, and anamino group; a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinylgroup, and a triazinyl group; and a phenyl group, a naphthyl group, ananthryl group, a fluorenyl group, a carbazolyl group, a pyridinyl group,a pyrimidinyl group, and a triazinyl group that are substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinylgroup, and a triazinyl group.

In an embodiment, in Formulae 3A-(1), 3A-(2), 3A-(3), 3A-(4), 3A-(5),3A-(6), 3A-(7), 3A-(8), and 3A-(9), R₁, to R_(5a), R_(1b) to R_(5b),R_(11a) to R_(14a), R_(11b) to R_(14b), R_(21a) to R_(28a), and R_(21b)to R_(28b)) each independently may be, e.g., a hydrogen atom, adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine, a hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group(for example, a methyl group, an ethyl group, an n-propyl group, ai-propyl group, an n-butyl group, a i-butyl group, a t-butyl group, apentyl group, a hexyl group, a heptyl group, an octyl group, a nonylgroup, a decyl group, or the like), a C₁-C₂₀ alkyl group substitutedwith at least one fluorine atom (for example, —CF₃), a C₁-C₂₀ alkoxygroup, a phenyl group, a naphthyl group, or an anthryl group.

For example, the organometallic compound may be represented by Formula3A-(1), 3A-(2), 3A-(4), 3A-(6), 3A-(8), or 3A-(9), whereinR_(1a)=R_(1b), R_(2a)=R_(2b)), R_(3a)=R_(3b), R_(4a)=R_(4b)),R_(5a)=R_(5b), R_(11a)=R_(11b), R_(12a)=R_(12b), R_(13a)=R_(13b),R_(14a)=R_(14b), R_(21a)=R_(21b), R_(22a)=R_(22b), R_(23a)=R_(23b),R_(24a)=R_(24b), R_(25a)=R_(25b), R_(26a)=R_(26b), R_(27a)=R_(27b), andR_(28a)=R_(28b).

The organometallic compound may be represented by Formula 4-(a) below.

In Formula 4-(a), M and L may be as set forth above, and m1 may be 0, 1,or 2.

In Formula 4-(a), X_(1a) may be N or C(R_(5a)); X_(1b) may be N orC(R_(5b)); and the above-description of R₁ may be used to describeR_(2a) to R_(5a), and R_(1b) to R_(5b)).

In Formula 4-(a), Y₁ may be i) a divalent linking group including atleast one of —O—, —S—, —N(Z₁)—, —[C(Z₂)(Z₃)]_(a)—, and—[Si(Z₄)(Z₅)]_(b)—, or ii) a single bond,

In —N(Z₁)—, —[C(Z₂)(Z₃)]_(a)—, and —[Si(Z₄)(Z₅)]_(b)—, Z₁ to Z₅ eachindependently may be a hydrogen atom, a deuterium atom, a halogen atom,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine, a hydrazone, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkyl groupsubstituted with at least one halogen atom, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₃-C₁₀ cycloalkenyl group, a C₃-C₁₀ heterocycloalkyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, or a C₂-C₆₀ heteroarylgroup, and a and b each independently may be an integer from 1 to 4.

In an embodiment, in —N(Z₁)—, —[C(Z₂)(Z₃)]_(a)—, and —[Si(Z₄)(Z₅)]_(b)—,Z₁ to Z₅ each independently may be, e.g., a C₁-C₂₀ alkyl group (forexample, a methyl group, an ethyl group, an n-propyl group, a i-propylgroup, an n-butyl group, a i-butyl group, a t-butyl group, a pentylgroup, a hexyl group, a heptyl group, an octyl group, a nonyl group, adecyl group, or the like), a C₁-C₂₀ alkyl group substituted with atleast —F (for example, —CF₃), a phenyl group, a naphthyl group, or ananthryl group, and a and b each independently may be 1 or 2.

For example, in Formula 4-(a), Y₁ may be —N(Z₁)—, wherein Z₁ may be atleast one of, e.g., a phenyl group, a naphthyl group, an anthryl group,a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinylgroup, and a triazinyl group; and a phenyl group, a naphthyl group, ananthryl group, a fluorenyl group, a carbazolyl group, a pyridinyl group,a pyrimidinyl group, and a triazinyl group that are substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, a C₁-C₁₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinylgroup, and a triazinyl group.

In some other embodiments, the organometallic compound may be anorganometallic compound represented by Formula 1 with n=3 and m=0. Thatis, the organometallic compound may include just three ligandsrepresented by Formula 1′. In an embodiment, in the organometalliccompound represented by Formula 1 with n=3 and m=0, M may be Ir, and X₁and R₁ to R₄ may be as set forth above.

In some other embodiments, the organometallic compound may be anorganometallic compound represented by Formula 1 wherein n=1 and m is aninteger from 1 to 4.

In an embodiment, the organometallic compound represented by Formula 1wherein n=1 and m is an integer from 1 to 4 may be an organometalliccompound represented by, e.g., one of the Formulae 5 to 8 below:

In Formulae 5 to 8, M, X1, R₁ to R₅, and L may be as set forth above,and m2 may be 0, 1, or 2.

In Formulae 5 to 8, X₁₂ and X_(16d) each independently may be N or C;and X₂₁ may be N or C(R₅₁); X₂₂ may be N or C(R₅₂); X₂₃ may be N orC(R₅₃); X₂₄ may be N or C(R₅₄); X₂₅ may be N or C(R₅₅); X₂₆ may be N orC(R₅₆); X₂₇ may be N or C(R₅₇); X₂₈ may be N or C(R₅₈); and X₂₉ may be Nor C(R₅₉); R₄₁, R₄₂, and R₅₁ to R₅₉ each independently may be a hydrogenatom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, a phosphoric acid group or a salt thereof, a substitutedor unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstitutedC₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynylgroup, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substitutedor unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₃-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅)(where Q₁₁ to Q₁₅ are each independently a hydrogen atom, a C₁-C₁₀ alkylgroup, a C₆-C₂₀ aryl group, or a C₂-C₂₀ heteroaryl group), or a bindingsite with an adjacent ligand via a single bond or divalent linkinggroup, wherein two adjacent substituents of R₄₁, R₄₂, and R₅₁ to R₅₉ areoptionally linked together to form a substituted or unsubstituted C₄-C₂₀alicyclic ring, a substituted or unsubstituted C₂-C₂₀ heteroalicyclicring, a substituted or unsubstituted C₆-C₂₀ aromatic ring, or asubstituted or unsubstituted C₂-C₂₀ heteroaromatic ring.

In Formulae 5 to 8, the above-description of R₁ may be used to describeR₄₁, R₄₂, and R₅₁ to R₅₉, and the above-description of the B ring may beused to describe “the substituted or unsubstituted C₄-C₂₀ alicyclicring, the substituted or unsubstituted C₂-C₂₀ heteroalicyclic ring, thesubstituted or unsubstituted C₆-C₂₀ aromatic ring, or the substituted orunsubstituted C₂-C₂₀ heteroaromatic ring.”

In an embodiment, the organometallic compound may be represented byFormula 5-(1), 5-(2), 5-(3), or 5-(4) below:

In Formulae 5-(1) to 5-(4), M, X₁, R₁ to R₅, L, m2, X₂₁ to X₂₆, R₄₁, andR₅₁ to R₅₉ may be as set forth above, and the above-description of R₁₁may be used to describe R₆₁ to R₆₈, and R₇₁ to R₇₄.

In an embodiment, in Formulae 5-(1) to 5-(4), X₂₁ may be N or C(R₅₁);X₂₂ may be N or C(R₅₂); X₂₃ may be N or C(R₅₃); X₂₄ may be N or C(R₅₄);X₂₅ may be N or C(R₅₅); and X₂₆ may be N or C(R₅₆); R₄₁ to R₅₆, R₆₁ toR₆₈, and R₇₁ to R₇₄ each independently may be, e.g., a hydrogen atom, adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine, a hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, and a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group and a C₁-C₁₀alkoxy group that are substituted with at least one of a deuterium atom,a halogen atom, a hydroxyl group, a cyano group, a nitro group, and anamino group; a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinylgroup, and a triazinyl group; and a phenyl group, a naphthyl group, ananthryl group, a fluorenyl group, a carbazolyl group, a pyridinyl group,a pyrimidinyl group, and a triazinyl group that are substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinylgroup, and a triazinyl group.

In some other embodiments, the organometallic compound may berepresented by Formula 5-(a), 6-(a), or 7-(a) below:

In Formulae 5-(a), 6-(a), and 7-(a), M, X₁, R₂ to R₅, L, m2, X₂₁ to X₂₇,R₄₁, and R₅₁ to R₅₉ may be as set forth above. X₁₂ may be C or N;

In Formulae 5-(a), 6-(a), and 7-(a), Y₂ may be a single bond or adivalent linking group including at least one of —O—, —S—, —N(Z₁₁)—,—[C(Z₁₂)(Z₁₃)]c-, and —[Si(Z₁₄)(Z₁₅)]d-, wherein Z₁₁ to Z₁₅ eachindependently may be, e.g., a hydrogen atom, a deuterium atom, a halogenatom, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine, a hydrazone, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, C₁-C₆₀ alkyl group, a C₁-C₆₀ alkyl groupsubstituted with at least one halogen atom, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₃-C₁₀ cycloalkenyl group, a C₃-C₁₀ heterocycloalkyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, or a C₂-C₆₀ heteroarylgroup, and c and d each independently may be an integer from 1 to 4.

The organometallic compound may be, for example, one of Compounds 1 to68 below:

In the organometallic compound of Formula 1, R₁ may be located between afirst nitrogen and a second nitrogen, and thus the R₁ may have acidiccharacteristics (as illustrated in Formula 1″ below), which may allowfor improved thermal stability.

For example, in the organometallic compound represented by Formula 3,R_(1a) may be located between a first nitrogen and a second nitrogen,and thus the organometallic compound may have acidic characteristics,thereby allowing for the formation of an intermolecular hydrogen bondwith a third nitrogen of an adjacent ligand (as illustrated in Formula3″ below).

Therefore, the organometallic compounds according to one or more of theabove embodiments may have improved thermal stability. Accordingly, anorganic light-emitting device including the organometallic compoundsaccording to one or more of the above embodiments may have improvedproperties (e.g., a low driving voltage, a high luminance, a highefficiency, a long lifetime, and the like).

The organometallic compound of Formula 1 may be synthesized using asuitable organic synthesis method. A synthesis method of theorganometallic compound of Formula 1 will be understood by those skilledin the art from the examples that will be described below.

The organometallic compound of Formula 1 may be used between a pair ofelectrodes of an organic light-emitting device, for example, in anemission layer of the organic light-emitting device.

According to an embodiment, an organic light-emitting device may includea first electrode, a second electrode disposed opposite to the firstelectrode, and an organic layer disposed between the first electrode andthe second electrode, wherein the organic layer may include at least oneof the organometallic compounds of Formula 1 described above.

As used herein, phrases like, for example, “the organic layer includesat least one organometallic compound” mean that “the organic layerincludes one of the organometallic compounds of Formula 1 above, or atleast two different organometallic compounds of Formula 1 above.”

The organic layer may include at least one layer selected from among ahole injection layer, a hole transport layer, a functional layer havingboth hole injection and hole transport capabilities (hereinafter,“H-functional layer”), a buffer layer, an electron blocking layer, anemission layer, a hole blocking layer, an electron transport layer, anelectron injection layer, and a functional layer having both electroninjection and electron transport capabilities (hereinafter,“E-functional layer”).

The term “organic layer” as used herein may refer to a single layerand/or a plurality of layers disposed between the first and secondelectrodes of the organic light-emitting device.

The organic layer may include an emission layer, and the emission layermay include the organometallic compound of Formula 1 described above.The emission layer including the organometallic compound may emit lightgenerated based on the mechanism of phosphorescence.

In an embodiment, the organometallic compound in the emission layer ofthe organic light-emitting device may serve as a dopant, and theemission layer may further include a carbazole-based compound as a host.

An example of the carbazole-based compound available as a host is acompound represented by Formula 10 below:

In Formula 10, Ar₁ may be a substituted or unsubstituted C₁-C₆₀alkylenegroup, a substituted or unsubstituted C₂-C₆₀ alkenylene group, —N(R₁₀₀)—(where R₁₀₀ may be a substituted or unsubstituted C₆-C₆₀aryl group, or asubstituted or unsubstituted C₂-C₆₀ heteroaryl group), a substituted orunsubstituted C₆-C₆₀ arylene group, or a substituted or unsubstitutedC₂-C₆₀heteroarylene group; p may be an integer from 0 to 10; R₉₁ to R₉₆each independently may be a hydrogen atom, a deuterium atom, a halogenatom, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine, a hydrazone, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenylgroup, a substituted or unsubstituted C₃-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, or a substituted or unsubstituted C₂-C₆₀heteroaryl group, wherein adjacent two substituents of R₉₁ to R₉₆ areoptionally linked together to form a substituted or unsubstituted C₄-C₂₀alicyclic group, a substituted or unsubstituted C₂-C₂₀ heteroalicyclicgroup, a substituted or unsubstituted C₆-C₂₀ aromatic ring, or asubstituted or unsubstituted C₂-C₂₀ heteroaromatic ring; and q, r, s, t,u, and v each independently may be an integer from 1 to 4.

In Formula 10, Ar₁ may be a C₁-C₅ alkylene group, a C₂-C₅ alkenylenegroup, —C(═O)—, or —N(R₁₀₀)—, wherein R₁₀₀ may be at least one of aphenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, and atriazinyl group; and a phenyl group, a naphthyl group, an anthryl group,a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinylgroup, and a triazinyl group that are substituted with at least one of adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, a C₁-C₁₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, and atriazinyl group.

In Formula 10, R₉₁ to R₉₆ each independently may be one of a hydrogenatom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, and a C₁-C₂₀ alkoxy group; and a C₁-C₂₀ alkyl group and aC₁-C₂₀ alkoxy group that are substituted with at least one of adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, and an amino group.

The carbazole-based compound may be, e.g., one of the followingcompounds H1-H30:

The FIGURE illustrates a schematic sectional view of an organiclight-emitting device 10 according to an embodiment. Hereinafter, astructure of an organic light-emitting device according to an embodimentand a method of manufacturing the same will be described with referenceto the FIGURE.

The substrate 11 may be a suitable substrate for use in an organiclight-emitting device. In an embodiment, the substrate 11 may be a glasssubstrate or a transparent plastic substrate with strong mechanicalstrength, thermal stability, transparency, surface smoothness, ease ofhandling, and water resistance.

A first electrode 13 may be formed by depositing or sputtering a firstelectrode-forming material on a surface of the substrate 11. When thefirst electrode 13 is an anode, a material having a high work functionmay be used as the first electrode-forming material to facilitate holeinjection. The first electrode 13 may be a reflective electrode or atransmission electrode. Suitable first electrode-forming materials maybe transparent and conductive materials such as ITO, IZO, SnO₂, and ZnO.The first electrode 13 may be formed as a reflective electrode usingmagnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca),magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or the like.

The first electrode 13 may have a single-layer structure or amulti-layer structure including at least two layers. For example, thefirst electrode 13 may have a three-layered structure of ITO/Ag/ITO.

The organic layer 15 may be disposed on the first electrode 13.

The organic layer 15 may include a hole injection layer (HIL), a holetransport layer (HTL), a buffer layer, an emission layer (EML), anelectron transport layer (ETL), and an electron injection layer (EIL).

The HIL may be formed on the first electrode 13 by vacuum deposition,spin coating, casting, Langmuir-Blodgett (LB) deposition, or the like.

When the HIL is formed using vacuum deposition, vacuum depositionconditions may vary according to the compound that is used to form theHIL, and the desired structure and thermal properties of the HIL to beformed. For example, vacuum deposition may be performed at a temperatureof about 100° C. to about 500° C., a pressure of about 10-8 torr toabout 10-3 torr, and a deposition rate of about 0.01 to about 100 Å/sec.

When the HIL is formed using spin coating, the coating conditions mayvary according to the compound that is used to form the HIL, and thedesired structure and thermal properties of the HIL to be formed. Forexample, the coating rate may be in the range of about 2000 rpm to about5000 rpm, and a temperature at which heat treatment may be performed toremove a solvent after coating may be in the range of about 80° C. toabout 200° C.

The HIL may be formed of a suitable material for a HIL. For example, thematerial that can be used to form the HIL areN,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine,(DNTPD), a phthalocyanine compound such as copper phthalocyanine,4,4′,4″-tris (3-methylphenylphenylamino) triphenylamine (m-MTDATA),N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB), TDATA, 2T-NATA,polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (Pani/CSA), andpolyaniline)/poly(4-styrenesulfonate (PANI/PSS).

The thickness of the HIL may be about 100 Å to about 10000 Å, and in anembodiment, may be from about 100 Å to about 1000 Å. When the thicknessof the HIL is within these ranges, the HIL may have good hole injectingability without a substantial increase in driving voltage.

Then, a HTL may be formed on the HIL by using vacuum deposition, spincoating, casting, Langmuir-Blodgett (LB) deposition, or the like. Whenthe HTL is formed using vacuum deposition or spin coating, theconditions for deposition and coating may be similar to those for theformation of the HIL, though the conditions for the deposition andcoating may vary according to the material that is used to form the HTL.

Examples of suitable HTL forming materials are carbazole derivatives,such as N-phenylcarbazole or polyvinylcarbazole,N,N′-bis(3-methylphenyl)-N,N-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD),4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), andN,N′-di(1-naphthyl)-N,N′-diphenylbenzidine) (NPB).

The thickness of the HTL may be about 50 Å to about 2000 Å, and forexample, about 100 Å to about 1500 Å. When the thickness of the HTL iswithin these ranges, the HTL may have good hole transporting abilitywithout a substantial increase in driving voltage.

The H-functional layer (having both hole injection and hole transportcapabilities) may contain at least one material from each group of thehole injection layer materials and hole transport layer materials. Thethickness of the H-functional layer may be from about 500 Å to about10,000 Å, and in an embodiment, may be from about 100 Å to about 1,000Å. When the thickness of the H-functional layer is within these ranges,the H-functional layer may have good hole injection and transportcapabilities without a substantial increase in driving voltage.

In an embodiment, at least one of the HIL, HTL, and H-functional layermay include at least one of a compound of Formula 300 below and acompound of Formula 301 below:

In Formula 300, Ar₁₀₁ and Ar₁₀₂ each independently may be a substitutedor unsubstituted C₆-C₆₀ arylene group. In an embodiment, Ar₁₀₁ and Ar₁₀₂each independently may be one of a phenylene group, a pentalenylenegroup, an indenylene group, a naphthylene group, an azulenylene group, aheptalenylene group, an acenaphthylene group, a fluorenylene group, aphenalenylene group, a phenanthrenylene group, an anthracenylene group,a fluoranthenylene group, a triphenylenylene group, a pyrenylenylenegroup, a chrysenylene group, a naphthacenylene group, a picenylenegroup, a perylenylene group, and a pentacenylene group; and a phenylenegroup, a pentalenylene group, an indenylene group, a naphthylene group,an azulenylene group, a heptalenylene group, an acenaphthylene group, afluorenylene group, a phenalenylene group, a phenanthrenylene group, ananthracenylene group, a fluoranthenylene group, a triphenylenylenegroup, a pyrenylenylene group, a chrysenylene group, a naphthacenylenegroup, a picenylene group, a perylenylene group, and a pentacenylenegroup that are substituted with at least one of a deuterium atom, ahalogen atom, a hydroxyl group, a nitro group, a cyano group, an aminogroup, an amidino group, hydrazine, hydrazone, a carboxyl group or saltthereof, a sulfuric acid group or salt thereof, a phosphoric acid groupor salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₃-C₁₀ heterocycloalkyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, and a C₂-C₆₀ heteroaryl group.

In Formula 300, x_(a) and x_(b) each independently may be an integerfrom 0 to 5, for example, may be 0, 1, or 2. For example, x_(a) may be1, and x_(b) may be 0.

In Formulae 300 and 301, R₁₀₁ to R₁₀₈, R₁₁₁ to R₁₁₉, and R₁₂₁ to R₁₂₄each independently may be a hydrogen atom, a deuterium atom, a halogenatom, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine, a hydrazone, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀cycloalkyl group, a substituted or unsubstituted C₅-C₆₀ aryl group, asubstituted or unsubstituted C₅-C₆₀ aryloxy group, or a C₅-C₆₀ arylthiogroup.

In an embodiment, R₁₀₁ to R₁₀₈, R₁₁₁ to R₁₁₉, and R₁₂₁ to R₁₂₄ eachindependently may be one of a hydrogen atom; a deuterium atom; a halogenatom; a hydroxyl group; a cyano group; a nitro group; an amino group; anamidino group; a hydrazine; a hydrazone; a carboxyl group or a saltthereof; a sulfonic acid group or a salt thereof; a phosphoric acidgroup or a salt thereof; a C₁-C₁₀ alkyl group (for example, a methylgroup, an ethyl group, a propyl group, a butyl group, a pentyl group, ahexyl group, or the like); a C₁-C₁₀ alkoxy group (for example, a methoxygroup, an ethoxy group, a propoxy group, a butoxy group, a pentoxygroup, or the like); a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group thatare substituted with at least one of a deuterium atom, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, asulfonic acid group or a salt thereof, and a phosphoric acid group or asalt thereof; a phenyl group; a naphthyl group; an anthryl group; afluorenyl group; a pyrenyl group; and a phenyl group, a naphthyl group,an anthryl group, a fluorenyl group, and a pyrenyl group that aresubstituted with at least one of a deuterium atom, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof; a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxy group.

In Formula 300, R₁₀₉ may be one of a phenyl group, a naphthyl group, ananthryl group, a biphenyl group, and a pyridyl group; and a phenylgroup, a naphthyl group, an anthryl group, a biphenyl group, and apyridyl group that are substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a substituted or unsubstitutedC₁-C₂₀ alkyl group, and a substituted or unsubstituted C₁-C₂₀ alkoxygroup.

In an embodiment, the compound of Formula 300 may be a compoundrepresented by Formula 300A below:

In Formula 300A, R₁₀₁, R₁₁₀, R₁₂₁, and R₁₀₉ may be as set forth above.

In an embodiment, at least one of the HIL, HTL, and H-functional layermay include, e.g., at least one of compounds represented by Formulae 301to 320 below:

At least one of the HIL, HTL, and H-functional layer may further includea charge-generating material for improved layer conductivity, inaddition to a suitable hole injecting material, hole transport material,and/or material having both hole injection and hole transportcapabilities as described above.

The charge-generating material may be, for example, a p-dopant. Thep-dopant may be, for example, one of quinine derivatives, metal oxides,and compounds with a cyano group. Examples of the p-dopant are quinonederivatives such as tetracyanoquinonedimethane (TCNQ),2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), andthe like; metal oxides such as tungsten oxide, molybdenum oxide, and thelike; and cyano-containing compounds such as Compound 200 below.

When the hole injection layer, hole transport layer, or H-functionallayer further includes a charge-generating material, thecharge-generating material may be homogeneously dispersed orunhomogeneously distributed in the layer.

A buffer layer may be disposed between at least one of the HIL, HTL, andH-functional layer, and the EML. The buffer layer may compensate for anoptical resonance distance of light according to a wavelength of thelight emitted from the EML, and thus may increase efficiency. The bufferlayer may include a suitable hole injecting material or holetransporting material. In some other embodiments, the buffer layer mayinclude the same material as one of the materials included in the HIL,HTL, and H-functional layer that underlie the buffer layer.

Then, an EML may be formed on the HTL, H-functional layer, or bufferlayer by vacuum deposition, spin coating, casting, Langmuir-Blodget (LB)deposition, or the like. When the EML is formed using vacuum depositionor spin coating, the deposition and coating conditions may be similar tothose for the formation of the HIL, though the conditions for depositionand coating may vary according to the material that is used to form theEML.

The EML may include the organometallic compound (as a dopant)represented by Formula 1 above, and a host.

An amount of the dopant (i.e., the organometallic compound of Formula 1)in the EML may be selected from a range of, e.g., about 0.01 to about 15parts by weight based on 100 parts by weight of the host.

The thickness of the EML may be from about 100 Å to about 1000 Å, and inan embodiment, may be from about 200 Å to about 600 Å. When thethickness of the EML is within these ranges, the EML may have good lightemitting ability without a substantial increase in driving voltage.

A hole blocking layer (HBL) may be formed on the EML to preventdiffusion of triplet excitons or holes into the ETL. When the HBL isformed using vacuum deposition or spin coating, the conditions fordeposition and coating may be similar to those for the formation of theHIL, although the conditions for deposition and coating may varyaccording to the material that is used to form the HBL. A suitablehole-blocking material may be used. Examples of hole-blocking materialsare oxadiazole derivatives, triazole derivatives, and phenanthrolinederivatives. For example, bathocuproine (BCP) represented by thefollowing formula may be used as a material for forming the HBL.

The thickness of the HBL may be from about 200 Å to about 1000 Å, and inan embodiment, may be from about 30 Å to about 300 Å. When the thicknessof the HBL is within these ranges, the HBL may have improved holeblocking ability without a substantial increase in driving voltage.

Then, an ETL may be formed on the HBL by a suitable method, for example,vacuum deposition, spin coating, or casting. When the ETL is formedusing vacuum deposition or spin coating, the deposition and coatingconditions may be similar to those for the formation of the HIL, thoughthe deposition and coating conditions may vary according to a compoundthat is used to form the ETL. A material for forming the ETL may be asuitable material that can stably transport electrons injected from anelectron injecting electrode (cathode). Examples of materials forforming the ETL are a quinoline derivative, such astris(8-quinolinorate)aluminum (Alq3), TAZ, BAlq, berylliumbis(benzoquinolin-10-olate) (Bebq2), 9,10-di(naphthalene-2-yl)anthracene(ADN), Compound 201, and Compound 202.

The thickness of the ETL may be from about 100 Å to about 1000 Å, and inan embodiment, may be from about 150 Å to about 500 Å. When thethickness of the ETL is within these ranges, the ETL may havesatisfactory electron transporting ability without a substantialincrease in driving voltage.

In an embodiment the ETL may further include a metal-containingmaterial, in addition to a suitable electron-transporting organiccompound.

The metal-containing material may include a lithium (Li) compound.Examples of the Li compound are lithium quinolate (LiQ) and Compound 203below:

Then, an EIL, which may facilitate injection of electrons from thecathode, may be formed on the ETL. A suitable electron-injectingmaterial may be used to form the EIL.

Examples of materials for forming the EIL are LiF, NaCl, CsF, Li₂O, andBaO. The deposition and coating conditions for forming the EIL may besimilar to those for the formation of the HIL, though the deposition andcoating conditions may vary according to the material that is used toform the EIL.

The thickness of the EIL may be from about 1 Å to about 100 Å, and in anembodiment, may be from about 3 Å to about 90 Å. When the thickness ofthe EIL is within these ranges, the EIL may have satisfactory electroninjection ability without a substantial increase in driving voltage.

A second electrode 17 may be disposed on the organic layer 15. Thesecond electrode 17 may be a cathode that is an electron injectionelectrode. A material for forming the second electrode 17 may be ametal, an alloy, an electro-conductive compound, which may have a lowwork function, or a mixture thereof. In an embodiment, the secondelectrode 17 may be a transmission (e.g., transparent) electrode and maybe formed using a thin film of Li, Mg, Al, Al—Li, Ca, Mg—In, Mg—Ag, orthe like. In an embodiment, to manufacture a top-emission light-emittingdevice, the transmission electrode may be formed of indium tin oxide(ITO) or indium zinc oxide (IZO).

The above description of the organic light-emitting device illustratedin the FIGURE is given by way of example.

The following Examples and Comparative Examples are provided in order tohighlight characteristics of one or more embodiments, but it will beunderstood that the Examples and Comparative Examples are not to beconstrued as limiting the scope of the embodiments, nor are theComparative Examples to be construed as being outside the scope of theembodiments. Further, it will be understood that the embodiments are notlimited to the particular details described in the Examples andComparative Examples.

Examples of the unsubstituted C₁-C₆₀ alkyl group used herein are linearor branched C₁-C₆₀ alkyl groups, such as methyl group, ethyl group,propyl group, isobutyl group, sec-butyl group, pentyl group, iso-amylgroup, hexyl group, or the like. In the substituted C₁-C₆₀ alkyl group,at least one hydrogen atom of the unsubstituted C₁-C₆₀ alkyl groupdescribed above may be substituted with a deuterium atom, a halogenatom, a hydroxyl group, a nitro group, a cyano group, an amino group, anamidino group, a hydrazine, a hydrazone, a carboxyl group or saltsthereof, a sulfonic acid group or salts thereof, a phosphoric acid groupor salts thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₆-C₆₀ aryl group, a C₂-C₆₀ heteroaryl group,—N(Q₁₁)(Q₁₂), or —Si(Q₁₃)(Q₁₄)(Q₁₅), wherein Q₁ to Q₁₅ eachindependently may be selected from the group of a hydrogen atom, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₅-C₆₀ aryl group, and a C₂-C₆₀ heteroaryl group. The unsubstitutedC₁-C₆₀ alkoxy group may be a group represented by —OA, wherein A is anunsubstituted C₁-C₆₀ alkyl group described above.

Examples of the unsubstituted C₁-C₆₀ alkoxy group are a methoxy group,an ethoxy group, and an isopropyloxy group. At least one of the hydrogenatoms in the alkoxy group may be substituted with the substituentsdescribed above in conjunction with the substituted C₁-C₆₀ alkyl group.

As used herein, the unsubstituted C₂-C₆₀ alkenyl group may be ahydrocarbon chain having a carbon-carbon double bond in the center or ata terminal of the unsubstituted C₂-C₆₀ alkyl group. Examples of theunsubstituted C₂-C₆₀ alkenyl group are ethenyl group, propenyl group,and butenyl groups. At least one hydrogen atom in the unsubstitutedC₂-C₆₀ alkenyl group may be substituted with the substituents describedin conjunction with the substituted C₁-C₆₀ alkyl group.

The unsubstituted C₂-C₆₀ alkynyl group may be a hydrocarbon chain havingat least one carbon-carbon triple bond in the center or at a terminalthereof. Examples of the unsubstituted C₂-C₆₀ alkynyl group are anethenyl group, a propenyl group, a butenyl group, and the like. At leastone hydrogen atom in the alkynyl group may be substituted with thesubstituents described above in conjunction with the C₁-C₆₀ alkyl group.

The unsubstituted C₆-C₆₀ aryl group may be a monovalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms including atleast one aromatic ring. The unsubstituted C₆-C₆₀ arylene group may be abivalent group having a carbocyclic aromatic system having 6 to 60carbon atoms including at least one aromatic ring. When the aryl groupand the arylene group have at least two rings, they may be fused to eachother via a single bond. At least one hydrogen atom in the aryl groupand the arylene group may be substituted with the substituents describedabove in conjunction with the C₁-C₆₀ alkyl group.

Examples of the substituted or unsubstituted C₆-C₆₀ aryl group are aphenyl group, a C₁-C₁₀ alkylphenyl group (e.g., an ethylphenyl group), aC₁-C₁₀ alkylbiphenyl group (e.g., an ethylbiphenyl group), a halophenylgroup (e.g., an o-, m-, or p-fluorophenyl group and a dichlorophenylgroup), a dicyanophenyl group, a trifluoromethoxyphenyl group, an o-,m-, or p-tolyl group, an o-, m- or p-cumenyl group, a mesityl group, aphenoxyphenyl group, a (α,α-dimethylbenzene)phenyl group, a(N,N′-dimethyl)aminophenyl group, a (N,N′-diphenyl)aminophenyl group, apentalenyl group, an indenyl group, a naphthyl group, a halonaphthylgroup (e.g., a fluoronaphthyl group), a C₁-C₁₀ alkylnaphthyl group(e.g., a methylnaphthyl group), a C₁-C₁₀ alkoxynaphthyl group (e.g., amethoxynaphthyl group), an anthracenyl group, an azulenyl group, aheptalenyl group, an acenaphthylenyl group, a phenalenyl group, afluorenyl group, an anthraquinolyl group, a methylanthryl group, aphenanthryl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, an ethyl-chrysenyl group, a picenyl group, a perylenyl group, achloroperylenyl group, a pentaphenyl group, a pentacenyl group, atetraphenylenyl group, a hexaphenyl group, hexacenyl group, a rubicenylgroup, a coronenyl group, a trinaphthylenyl group, a heptaphenyl group,a heptacenyl group, a pyranthrenyl group, and an ovalenyl group.Examples of the substituted C₅-C₆₀ aryl group may be inferred based onthose of the unsubstituted C₅-C₆₀ aryl group and the substituted C₁-C₆₀alkyl group described above. Examples of the substituted orunsubstituted C₅-C₆₀ arylene group may be inferred based on thoseexamples of the substituted or unsubstituted C₅-C₆₀ aryl group describedabove.

The unsubstituted C₂-C₆₀ heteroaryl group may be a monovalent grouphaving at least one aromatic ring having at least one of the heteroatomsselected from the group of N, O, P, and S. The unsubstituted C₂-C₆₀heteroarylene group may be a divalent group having at least one aromaticring having at least one of the heteroatoms selected from the group ofN, O, P, and S. In this regard, when the heteroaryl group and theheteroarylene group have at least two rings, they may be fused to eachother via a single bond. At least one hydrogen atom in the heteroarylgroup and the heteroarylene group may be substituted with thosesubstituents described above in conjunction with the C₁-C₆₀ alkyl group.

Examples of the unsubstituted C₂-C₆₀ heteroaryl group are a pyrazolylgroup, an imidazolyl group, an oxazolyl group, a thiazolyl group, atriazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridinylgroup, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, acarbazolyl group, an indolyl group, a quinolinyl group, an isoquinolinylgroup, a benzoimidazolyl group, an imidazopyridinyl group and animidazopyrimidinyl group. Examples of the substituted C₂-C₆₀heteroarylene group may be inferred based on those examples of thesubstituted or unsubstituted C₂-C₆₀ arylene group described above.

The substituted or unsubstituted C₆-C₆₀ aryloxy group may be —OA₂(wherein A₂ may be a substituted or unsubstituted C₆-C₆₀ aryl groupdescribed above). The substituted or unsubstituted C₅-C₆₀ arylthio groupmay be —SA₃ (wherein A₃ may be a substituted or unsubstituted C₆-C₆₀aryl group described above).

SYNTHESIS EXAMPLES

Ligand 1 (L1) to Ligand 43 (L43)

Ligand Synthesis 1: Synthesis of Ligand 1 L1)

Ligand 1 (L1) was synthesized according to Reaction Scheme 1 below:

Synthesis of Intermediate 1(3)

Following adding 1.9 g (80.8 mmol) of NaH to 80 ml of dichlormethane,5.0 g (73.5 mmol) of pyrazole was added thereto at 0° C. and thenstirred for about 30 minutes. Afterward, 11.5 ml (80.8 mmol) of benzylchloroformate dissolved in 30 ml of dichloromethane was dropwise addedthereto at 0° C., and stirred for about 1 hour, then further at roomtemperature for about 3 hours. After completion of the reaction, 100 mlof saturated sodium hydrocarbonate was added thereto, followed byextraction with 50 ml of methylene chloride three times to obtain anorganic layer, which was then dried using magnesium sulfate, followed bydistillation under reduced pressure. The resulting product was separatedand purified using column chromatography to obtain 12.6 g (62.4 mmol,Yield: 85%) of Intermediate 1(3). This compound was identified usingliquid chromatography-mass spectroscopy (LC-MS).

LC-MS m/z=203 (M+H)+

Synthesis of Intermediate 1(2)

After dissolving 10.0 g (49.5 mmol) of Intermediate 1(3) in 80 ml ofanhydrous tetrahydrofuran, 25 ml (2.2M in THF, 54.5 mmol) of n-BuLi wasslowly added thereto at 0° C., and stirred at room temperature for about1 hour. After 1 hour, the temperature was lowered to about −78° C., 12.0ml (59.4 mmol) of isopropyl pinacol borate was slowly added to thereaction mixture, and stirred at −78° C. for about 15 minutes.Afterward, the temperature was slowly increased to 0° C., and thereaction mixture was further stirred for about 1 hour. After completionof the reaction, 100 ml of a saturated chloroammonium solution as addedthereto, and extracted with 100 ml of dichloromethane to obtain anorganic layer, which was then washed with 100 mL of distilled watertwice and dried using magnesium sulfate, followed by distillation underreduced pressure to obtain 9.7 g (29.7 mmol, Yield: 60%) of Intermediate1(2).

LC-MS m/z=329(M+H)+

Synthesis of Intermediate 1(1)

After dissolving 1.9 g (12.2 mmol) of 4-bromopyrimidine in 120 ml of amixed solvent of dioxolane and water (5:1) in a seal-tube, 5.0 g (36.6mmol) of potassium carbonate, 1.4 g (1.2 mmol) ofTetrakistriphenylphosphine Pd(0), and 8.0 g (24.4 mmol) of Intermediate1(2) were added thereto. The resulting reaction mixture was stirred at90° C. for a day. After completion of the reaction, 100 ml of distilledwater was added to the reaction product, followed by extraction with 100ml of dichloromethane to obtain an organic layer, which was then driedusing magnesium sulfate, and distilled under reduced pressure to obtain2.0 g (7.3 mmol, Yield: 60%) of Intermediate 1(1).

LC-MS m/z=280(M+H)+

Synthesis of Ligand 1 (L1)

After dissolving 2.0 g (7.3 mmol) of Intermediate 1(1) in 60 ml ofmethanol at room temperature, 0.2 g of Pd/C (10% w/w) was added theretoand stirred at room temperature for about 12 hours with hydrogen purgingAfter completion of the reaction, Pd/C was removed using CELITE toobtain an organic layer, which was then concentrated under reducedpressure. The resulting product was separated and purified using columnchromatography to obtain 1.0 g (6.9 mmol, Yield: 95%) of ligand 1 (L1).This compound was identified using LC-MS.

LC-MS m/z=203(M+14)+

Ligand Synthesis 2: Synthesis of Ligand 2 (L2)

Ligand 2 (L2) was synthesized according to Reaction Scheme 2 below:

Synthesis of Ligand 2 (L2)

After dissolving 2.0 g (12.6 mmol) of 4-bromopyrimidine in 80 ml of1,2-dimethoxyethane at room temperature, 1.4 g (1.2 mmol) oftetrakistriphenylphosphine Pd(0), and 4.6 g (18.9 mmol) of1H-indazol-3-ylboronic acid pinacol ester were added thereto. Theresulting reaction mixture was heated at about 90° C. for about 18 hoursunder reflux. After completion of the reaction, 100 ml of distilledwater was added to the reaction product, followed by extraction with 100ml of dichloromethane to obtain an organic layer, which was then driedusing magnesium sulfate, distilled under reduced pressure, and thenseparated and purified using column chromatography to obtain 1.1 g (5.7mmol, Yield: 45%) of ligand 2 (L2).

LC-MS m/z=197(M+H)+

Ligand Synthesis 3: Synthesis of Ligand 3 (L3)

Ligand 3 (L3) was synthesized according to Reaction Scheme 3 below:

0.8 g (3.2 mmol, Yield: 25%) of ligand 3 (L3) was synthesized in thesame manner as in the synthesis of ligand 2 (L2) (Ligand Synthesis 2),except that 4-bromoquinazoline, instead of 4-bromopyrimidine, was usedin synthesizing Ligand (L3).

LC-MS m/z=197(M+H)+

Ligand Synthesis 4: Synthesis of Ligand 4 (L4)

Ligand 4 (L4) was synthesized according to Reaction Scheme 4 below:

Synthesis of Intermediate 4(1)

Following adding 1.0 g (43.4 mmol) of NaH to 80 ml of anhydroustetrahydrofuran, 2.6 ml (34.8 mmol) of acetone was slowly added theretoat 0° C. After 1 hour, 4.0 g (29.0 mmol) of pyrimidine-4-carboxylic acidmethyl ester was slowly added thereto and heated under reflux at about80° C. for about 16 hours. After completion of the reaction, 30 ml ofdistilled water was added thereto, 2.5 ml of acetic was then slowlyadded and stirred at room temperature for about 30 minutes. After 30minutes, the resulting product was extracted with 100 ml ofdichloromethane five times to obtain an organic layer, which was driedusing magnesium sulfate and distilled under reduced pressure. Theresulting product was separated and purified using column chromatographyto obtain 1.8 g (11.0 mmol, Yield 38%) of Intermediate 4(1).

LC-MS m/z=165(M+H)+

Synthesis of Ligand 4 (L4)

After dissolving 1.8 g (11.0 mmol) of Intermediate 4(1) in 30 ml ofethanol at room temperature, 1.6 ml (55.0 mmol) of hydrazine hydrate wasadded thereto and heated under reflux at about 80° C. for about 18hours. After completion of the reaction, the reaction product wasconcentrated under reduced pressure and extracted with 80 ml ofdistilled water and 100 ml of dichloromethane to obtain an organiclayer, which was then dried using magnesium sulfate, distilled underreduced pressure, and then separated and purified using columnchromatography to obtain 1.5 g (9.3 mmol, Yield: 88%) of ligand 4 (L4).

LC-MS m/z=161(M+H)+

Ligand Synthesis 5: Synthesis of Ligand 5 (L5)

Ligand 5 (L5) was synthesized according to Reaction Scheme 5 below:

Ligand 5 (L5) was synthesized in the same manner (Yield: 25%) as in thesynthesis of ligand 4 (L4) (Ligand Synthesis 4), except that3,3-methylbutane-2-one, instead of acetone, was used in synthesizingIntermediate 4(1).

LC-MS m/z=189(M+H)+

Ligand Synthesis 6: Synthesis of Ligand 6 (L6)

Ligand 6 (L6) was synthesized according to Reaction Scheme 6 below:

Ligand 6 (L6) was synthesized in the same manner (Yield: 21%) as in thesynthesis of ligand 4 (L4) (Ligand Synthesis 4), except that3,3-dimethylbutane-2-one, instead of acetone, was used in synthesizingIntermediate 4(1).

LC-MS m/z=203(M+H)+

Ligand Synthesis 7: Synthesis of Ligand 7 (L7)

Ligand 7 (L7) was synthesized according to Reaction Scheme 7 below:

Ligand 7 (L7) was synthesized in the same manner (Yield: 63%) as in thesynthesis of ligand 4 (L4) (Ligand Synthesis 4), except that1,1,1-trifluoropropan-2-one, instead of acetone, was used insynthesizing Intermediate 4(1).

LC-MS m/z=215(M+H)+

Ligand Synthesis 8: Synthesis of Ligand 8 (L8)

Ligand 8 (L8) was synthesized according to Reaction Scheme 8 below:

Ligand 8 (L8) was synthesized in the same manner (Yield: 35%) as in thesynthesis of ligand 4 (L4) (Ligand Synthesis 4), except thatcyclohexanone, instead of acetone, was used in synthesizing Intermediate4(1).

LC-MS m/z=201(M+H)+

Ligand Synthesis 9: Synthesis of Ligand 9 (L9)

Ligand 9 (L9) was synthesized according to Reaction Scheme 9 below:

Ligand 9 (L9) was synthesized in the same manner (Yield: 43%) as in thesynthesis of ligand 4 (L4) (Ligand Synthesis 4), except that2,2-dimethylcyclohexanone, instead of acetone, was used in synthesizingIntermediate 4(1).

LC-MS m/z=229(M+H)+

Ligand Synthesis 10: Synthesis of Ligand 10 (L10)

Ligand 10 (L10) was synthesized according to Reaction Scheme 10 below:

Ligand 10 (L10) was synthesized in the same manner (Yield: 65%) as inthe synthesis of ligand 4 (L4) (Ligand Synthesis 4), except that camper,instead of acetone, was used in synthesizing Intermediate 4(1).

LC-MS m/z=254(M+H)+

Ligand Synthesis 11: Synthesis of Ligand 11 (L11)

Ligand 11 (L11) was synthesized according to Reaction Scheme 11 below:

Ligand 11 (L11) was synthesized in the same manner (Yield: 17%) as inthe synthesis of ligand 4 (L4) (Ligand Synthesis 4), except that methyl6-methylpyrimidine-4-caboxylate, instead of pyrimidine-4-carboxylic acidmethyl ester, was used in synthesizing Intermediate 4(1).

LC-MS m/z=175(M+H)+

Ligand Synthesis 12: Synthesis of Ligand 12 (L12)

Ligand 12 (L12) was synthesized according to Reaction Scheme 12 below:

Ligand 12 (L12) was synthesized in the same manner (Yield: 12%) as inthe synthesis of ligand 6 (L6) (Ligand Synthesis 6), except that methyl6-methylpyrimidine-4-caboxylate, instead of pyrimidine-4-carboxylic acidmethyl ester, was used in synthesizing Intermediate 6(1).

LC-MS m/z=217(M+H)+

Ligand Synthesis 13: Synthesis of Ligand 13 (L13)

Ligand 13 (L13) was synthesized according to Reaction Scheme 13 below:

Ligand 13 (L13) was synthesized in the same manner (Yield: 35%) as inthe synthesis of ligand 7 (L7) (Ligand Synthesis 7), except that methyl6-methylpyrimidine-4-caboxylate, instead of pyrimidine-4-carboxylic acidmethyl ester, was used in synthesizing Intermediate 7(1).

LC-MS m/z=229(M+H)+

Ligand Synthesis 14: Synthesis of Ligand 14 (L14)

Ligand 14 (L14) was synthesized according to Reaction Scheme 14 below:

Ligand 14 (L14) was synthesized in the same manner (Yield: 26%) as inthe synthesis of ligand 9 (L9) (Ligand Synthesis 9), except that methyl6-methylpyrimidine-4-caboxylate, instead of pyrimidine-4-carboxylic acidmethyl ester, was used in synthesizing Intermediate 9(1).

LC-MS m/z=243(M+H)+

Ligand Synthesis 15: Synthesis of Ligand 15 (L15)

Ligand 15 (L15) was synthesized according to Reaction Scheme 15 below:

Ligand 15 (L15) was synthesized in the same manner (Yield: 35%) as inthe synthesis of ligand 10 (L10) (Ligand Synthesis 10), except thatmethyl 6-methylpyrimidine-4-caboxylate, instead ofpyrimidine-4-carboxylic acid methyl ester, was used in synthesizingIntermediate 10(1).

LC-MS m/z=269(M+H)+

Ligand Synthesis 16: Synthesis of Ligand 16 (L16)

Ligand 16 (L16) was synthesized according to Reaction Scheme 16 below:

Ligand 16 (L16) was synthesized in the same manner (Yield: 14%) as inthe synthesis of ligand 4 (L4) (Ligand Synthesis 4), except that methyl6-methoxypyrimidine-4-carboxylate, instead of pyrimidine-4-carboxylicacid methyl ester, was used in synthesizing Intermediate 4(1).

LC-MS m/z=191(M+H)+

Ligand Synthesis 17: Synthesis of Ligand 17 (L17)

Ligand 17 (L17) was synthesized according to Reaction Scheme 17 below:

Ligand 17 (L17) was synthesized in the same manner (Yield: 12%) as inthe synthesis of ligand 6 (L6) (Ligand Synthesis 6), except that methyl6-methoxypyrimidine-4-carboxylate, instead of pyrimidine-4-carboxylicacid methyl ester, was used in synthesizing Intermediate 6(1).

LC-MS m/z=233(M+H)+

Ligand Synthesis 18: Synthesis of Ligand 18 (L18)

Ligand 18 (L18) was synthesized according to Reaction Scheme 18 below:

Ligand 18 (L18) was synthesized in the same manner (Yield: 25%) as inthe synthesis of ligand 7 (L7) (Ligand Synthesis 7), except that methyl6-methoxypyrimidine-4-carboxylate, instead of pyrimidine-4-carboxylicacid methyl ester, was used in synthesizing Intermediate 7(1).

LC-MS m/z=245(M+H)+

Ligand Synthesis 19: Synthesis of Ligand 19 (L19)

Ligand 19 (L19) was synthesized according to Reaction Scheme 19 below:

Ligand 19 (L19) was synthesized in the same manner (Yield: 22%) as inthe synthesis of ligand 9 (L9) (Ligand Synthesis 9), except that methyl6-methoxypyrimidine-4-carboxylate, instead of pyrimidine-4-carboxylicacid methyl ester, was used in synthesizing Intermediate 9(1).

LC-MS m/z=259(M+H)+

Ligand Synthesis 20: Synthesis of Ligand 20 (L20)

Ligand 20 (L20) was synthesized according to Reaction Scheme 20 below:

Ligand 20 (L20) was synthesized in the same manner (Yield: 30%) as inthe synthesis of ligand 10 (L10) (Ligand Synthesis 10), except thatmethyl 6-methoxypyrimidine-4-carboxylate, instead ofpyrimidine-4-carboxylic acid methyl ester, was used in synthesizingIntermediate 10(1).

LC-MS m/z=285(M+H)+

Ligand Synthesis 21: Synthesis of Ligand 21 (L21)

Ligand 21 (L21) was synthesized according to Reaction Scheme 21 below:

Ligand 21 (L21) was synthesized in the same manner (Yield: 26%) as inthe synthesis of ligand 4 (L4) (Ligand Synthesis 4), except that methyl6-(trifluoromethyl)pyrimidine-4-carboxylate, instead ofpyrimidine-4-carboxylic acid methyl ester, was used in synthesizingIntermediate 4(1).

LC-MS m/z=229(M+H)+

Ligand Synthesis 22: Synthesis of Ligand 22 (L22)

Ligand 22 (L22) was synthesized according to Reaction Scheme 22 below:

Ligand 22 (L22) was synthesized in the same manner (Yield: 24%) as inthe synthesis of ligand 6 (L6) (Ligand Synthesis 6), except that methyl6-(trifluoromethyl)pyrimidine-4-carboxylate, instead ofpyrimidine-4-carboxylic acid methyl ester, was used in synthesizingIntermediate 6(1).

LC-MS m/z=271(M+H)+

Ligand Synthesis 23: Synthesis of Ligand 23 (L23)

Ligand 23 (L23) was synthesized according to Reaction Scheme 23 below:

Ligand 23 (L23) was synthesized in the same manner (Yield: 37%) as inthe synthesis of ligand 7 (L7) (Ligand Synthesis 7), except that methyl6-(trifluoromethyl)pyrimidine-4-carboxylate, instead ofpyrimidine-4-carboxylic acid methyl ester, was used in synthesizingIntermediate 7(1).

LC-MS m/z=283(M+H)+

Ligand Synthesis 24: Synthesis of Ligand 24 (L24)

Ligand 24 (L24) was synthesized according to Reaction Scheme 24 below:

Ligand 24 (L24) was synthesized in the same manner (Yield: 42%) as inthe synthesis of ligand 10 (L10) (Ligand Synthesis 10), except thatmethyl 6-(trifluoromethyl)pyrimidine-4-carboxylate, instead ofpyrimidine-4-carboxylic acid methyl ester, was used in synthesizingIntermediate 10(1).

LC-MS m/z=323(M+H)+

Ligand Synthesis 25: Synthesis of Ligand 25 (L25)

Ligand 25 (L25) was synthesized according to Reaction Scheme 25 below:

Ligand 25 (L25) was synthesized in the same manner (Yield: 17%) as inthe synthesis of ligand 6 (L6) (Ligand Synthesis 6), except that methyl2-methylpyrimidine-4-caboxylate, instead of pyrimidine-4-carboxylic acidmethyl ester, was used in synthesizing Intermediate 6(1).

LC-MS m/z=217(M+H)+

Ligand Synthesis 26: Synthesis of Ligand 26 (L26)

Ligand 26 (L26) was synthesized according to Reaction Scheme 26 below:

Ligand 26 (L26) was synthesized in the same manner (Yield: 22%) as inthe synthesis of ligand 7 (L7) (Ligand Synthesis 7), except that methyl2-methylpyrimidine-4-caboxylate, instead of pyrimidine-4-carboxylic acidmethyl ester, was used in synthesizing Intermediate 7(1).

LC-MS m/z=229(M+H)+

Ligand Synthesis 27: Synthesis of Ligand 27 (L27)

Ligand 27 (L27) was synthesized according to Reaction Scheme 27 below:

Synthesis of Intermediate 27(1)

Following Adding 1.9 g (19.3 Mmol) of NatOBu (Sodium t-Butoxide) to 50ml of anhydrous tetrahydrofuran, 2.2 g (17.5 mmol) of2,2-dimethyl-3-pentanone was slowly added thereto at 0° C. After heatingthe mixture at about 60° C. for about 2 hours, 2.2 g (15.7 mmol) ofpyrimidine-4-carboxylic acid methyl ester was slowly added thereto andheated under reflux at about 80° C. for about 12 hours. After completionof the reaction, 50 ml of distilled water was added, and a 4N dilutedhydrochloric acid was added for neutralization, followed by extractionwith 100 ml of dichloromethane about three times to obtain an organiclayer, which was then dried using magnesium sulfate, distilled underreduced pressure, and then separated and purified using columnchromatography to obtain 0.6 g (2.5 mmol, Yield: 16%) of Intermediate27(1).

LC-MS m/z=223(M+H)+

Synthesis of Ligand 27 (L17)

After dissolving 0.5 g (2.5 mmol) of Intermediate 27(1) in 10 ml ofethanol at room temperature, 0.7 ml (55.0 mmol) of hydrazine hydrate wasadded thereto and heated under reflux at about 80° C. for about 18hours. After completion of the reaction, the reaction product wasconcentrated under reduced pressure and extracted with 30 ml ofdistilled water and 50 ml of dichloromethane to obtain an organic layer,which was then dried using magnesium sulfate and distilled under reducedpressure. The resulting product was separated and purified using columnchromatography to obtain 0.4 g (2.1 mmol, Yield: 85%) of ligand 27(L27).

LC-MS m/z=217(M+H)+

Ligand Synthesis 28: Synthesis of Ligand 28 (L28)

Ligand 28 (L28) was synthesized according to Reaction Scheme 28 below:

Ligand 28 (L28) was synthesized in the same manner (Yield: 12%) as inthe synthesis of ligand 27 (L27) (Ligand Synthesis 27), except that2,2,5,5-tetramethylhexan-3-one, instead of 2,2-dimethyl-3-pentanone, wasused in synthesizing Intermediate 27(1).

LC-MS m/z=259(M+H)+

Ligand Synthesis 29: Synthesis of Ligand 29 (L29)

Ligand 29 (L29) was synthesized according to Reaction Scheme 29 below:

Ligand 29 (L29) was synthesized in the same manner (Yield: 9%) as in thesynthesis of ligand 27 (L27) (Ligand Synthesis 27), except that2,2-dimethyl-4-(trifluoromethyl)-butanone, instead of2,2-dimethyl-3-pentanone, was used in synthesizing Intermediate 27(1).

LC-MS m/z=271(M+H)+

Ligand Synthesis 30: Synthesis of Ligand 30 (L30)

Ligand 30 (L30) was synthesized according to Reaction Scheme 30 below:

Ligand 30 (L30) was synthesized in the same manner (Yield: 10%) as inthe synthesis of ligand 27 (L27) (Ligand Synthesis 27), except that1,4,-di(trifluoromethyl)-2-butanone, instead of2,2,-dimethyl-3-pentanone, was used in synthesizing Intermediate 27(1).

LC-MS m/z=283(M+H)+

Ligand Synthesis 31: Synthesis of Ligand 31 (L31)

Ligand 31 (L31) was synthesized according to Reaction Scheme 31 below:

Synthesis of Intermediate 31(2)

Following dissolving 25.0 g (143.6 mmol) of 4-quinazoline-carboxylicacid in 100 ml of methanol, 5 ml of sulfuric acid (conc.) was addedthereto, and heated under reflux at about 80° C. for about 18 hours.After completion of the reaction, the reaction mixture was concentratedunder reduced pressure, and then dissolved in 100 ml of dichloromethane.A saturated sodium hydrocarbonate solution was slowly added thereto at0° C. for basification, followed by extraction to obtain an organiclayer, which was then dried using magnesium sulfate, and distilled underreduced pressure to obtain 26.0 g (137.8 mmol, Yield: 96%) ofIntermediate 31(2).

LC-MS m/z=189(M+H)+

Synthesis of Intermediate 31(1)

Following adding 1.0 g (43.4 mmol) of NaH to 80 ml of anhydroustetrahydrofuran, 2.6 ml (34.8 mmol) of acetone was slowly added theretoat 0° C. After 1 hour, 5.5 g (29.0 mmol) of Intermediate 31(2) wasslowly added thereto and heated under reflux at about 80° C. for about16 hours. After completion of the reaction, 30 ml of distilled water wasadded, and a 4N diluted hydrochloric acid solution was slowly addedthereto for neutralization. The resulting neutralized reaction mixturewas extracted with 100 ml of dichloromethane about five times to obtainan organic layer, which was dried using magnesium sulfate and distilledunder reduced pressure. The resulting product was separated and purifiedusing column chromatography to obtain 3.3 g (15.1 mmol, Yield 52%) ofIntermediate 31(1).

LC-MS m/z=215(M+H)+

Synthesis of Ligand 31 (L31)

After dissolving 3.0 g (13.9 mmol) of Intermediate 31(1) in 50 ml ofethanol at room temperature, 4.0 ml (140.0 mmol) of hydrazine hydratewas added thereto and heated under reflux at about 80° C. for about 18hours. After completion of the reaction, the reaction product wasconcentrated under reduced pressure and extracted with 80 ml ofdistilled water and 100 ml of dichloromethane to obtain an organiclayer, which was then dried using magnesium sulfate, distilled underreduced pressure, and then separated and purified using columnchromatography to obtain 2.2 g (10.4 mmol, Yield: 75%) of ligand 31(L31).

LC-MS m/z=211(M+H)+

Ligand Synthesis 32: Synthesis of Ligand 32 (L32)

Ligand 32 (L32) was synthesized according to Reaction Scheme 32 below:

Ligand 32 (L32) was synthesized in the same manner (Yield: 25%) as inthe synthesis of ligand 31 (L31) (Ligand Synthesis 31), except that3,3-dimethylbutane-2-one, instead of acetone, was used in synthesizingIntermediate 31(1).

LC-MS m/z=253(M+H)+

Ligand Synthesis 33: Synthesis of Ligand 33 (L33)

Ligand 33 (L33) was synthesized according to Reaction Scheme 33 below:

Ligand 33 (L33) was synthesized in the same manner (Yield: 22%) as inthe synthesis of ligand 31 (L31) (Ligand Synthesis 31), except that1,1,1-trifluoropropan-2-one, instead of acetone, was used insynthesizing Intermediate 31(1).

LC-MS m/z=265(M+H)+

Ligand Synthesis 34: Synthesis of Ligand 34 (L31)

Ligand 34 (L34) was synthesized according to Reaction Scheme 34 below:

Ligand 34 (L34) was synthesized in the same manner (Yield: 20%) as inthe synthesis of ligand 31 (L31) (Ligand Synthesis 31), except thatcyclohexanone, instead of acetone, was used in synthesizing Intermediate31(1).

LC-MS m/z=251(M+H)+

Ligand Synthesis 35: Synthesis of Ligand 35 (L35)

Ligand 35 (L35) was synthesized according to Reaction Scheme 35 below:

Ligand 35 (L35) was synthesized in the same manner (Yield: 22%) as inthe synthesis of ligand 31 (L31) (Ligand Synthesis 31), except that2,2-dimethylbutane-2-one, instead of acetone, was used in synthesizingIntermediate 31(1).

LC-MS m/z=279(M+H)+

Ligand Synthesis 36: Synthesis of Ligand 36 (L36)

Ligand 36 (L36) was synthesized according to Reaction Scheme 36 below:

Ligand 36 (L36) was synthesized in the same manner (Yield: 22%) as inthe synthesis of ligand 31 (L31) (Ligand Synthesis 31), except thatcamphor, instead of acetone, was used in synthesizing Intermediate31(1).

LC-MS m/z=305(M+H)+

Ligand Synthesis 37: Synthesis of Ligand 37 (L37)

Ligand 37 (L37) was synthesized according to Reaction Scheme 37 below:

Ligand 37 (L37) was synthesized in the same manner (Yield: 18%) as inthe synthesis of ligand 31 (L31) (Ligand Synthesis 31), except that2,2-dimethylbutane-3-one, instead of acetone, was used in synthesizingIntermediate 31(1).

LC-MS m/z=267(M+H)+

Ligand Synthesis 38: Synthesis of Ligand 38 (L38)

Ligand 38 (L38) was synthesized according to Reaction Scheme 38 below:

Ligand 38 (L38) was synthesized in the same manner (Yield: 20%) as inthe synthesis of ligand 31 (L31) (Ligand Synthesis 31), except that2,2-dimethyl-4-(trifluoromethyl)butan-3-one, instead of acetone, wasused in synthesizing Intermediate 31(1).

LC-MS m/z=321(M+H)+

Ligand Synthesis 39: Synthesis of Ligand 39 (L39)

Ligand 39 (L39) was synthesized according to Reaction Scheme 39 below:

Synthesis of Intermediate 39(4)

Following adding 2.1 g (86.8 mmol) of NaH to 120 ml of anhydroustetrahydrofuran, 8.7 ml (69.6 mmol) of 1,1,1-trifluoropropan-2-one wasslowly added thereto at 0° C. After 1 hour, 12.6 g (58.0 mmol) of methyl2-bromopyrimidine-4-carboxylate was slowly added thereto and heatedunder reflux at about 80° C. for about 16 hours. After completion of thereaction, 100 ml of distilled water was added, and a 1N dilutedhydrochloric acid solution was slowly added thereto and stirred at roomtemperature for about 30 minutes until the reaction mixture wasneutralized. After 30 minutes, the resulting product was extracted with100 ml of dichloromethane about five times to obtain an organic layer,which was then dried using magnesium sulfate and distilled under reducedpressure. The resulting product was separated and purified using columnchromatography to obtain 5.3 g (18.6 mmol, Yield 32%) of Intermediate39(4).

LC-MS m/z=297(M+H)+

Synthesis of Intermediate 39(3)

After dissolving 3.0 g (10.4 mmol) of Intermediate 39(4) in 30 ml ofethanol at room temperature, 2.6 ml (100.0 mmol) of hydrazine hydratewas added thereto and heated under reflux at about 80° C. for about 18hours. After completion of the reaction, the reaction product wasconcentrated under reduced pressure, and then extracted with 80 ml ofdistilled water and 100 ml of dichloromethane to obtain an organiclayer, which was then dried using magnesium sulfate and distilled underreduced pressure. The resulting product was separated and purified usingcolumn chromatography to obtain 2.1 g (7.5 mmol, Yield 72%) ofIntermediate 39(3).

LC-MS m/z=293(M+H)+

Synthesis of Intermediate 39(2)

Following adding 0.2 g (9.0 mmol) of NaH to 120 ml of anhydroustetrahydrofuran, 2.1 g (7.5 mmol) of Intermediate 39(2) was slowly addedthereto at 0° C. After 30 minutes, 1.5 ml (8.3 mmol) of2-(trimethylsilyl)ethoxymethyl chloride was slowly added thereto andstirred at room temperature for about two days. After completion of thereaction, the reaction product was extracted with 100 ml of distilledwater and 100 ml of dichloromethane to obtain an organic layer, whichwas then dried using magnesium sulfate and distilled under reducedpressure. The resulting product was separated and purified using columnchromatography to obtain 2.7 g (6.6 mmol, Yield 88%) of Intermediate39(2).

LC-MS m/z=423(M+H)+

Synthesis of Intermediate 39(1)

Following dissolving 2.7 g (6.6 mmol) of Intermediate 39(2) in 60 ml oftoluene, 0.05 g (0.05 mmol) of tris(dibenzylideneacetone)dipalladium(0),0.2 ml (2.6 mmol) of aniline, 0.06 g (0.1 mmol) of1,1′-bis(diphenylphospino)ferrocene, and 0.6 g (6.6 mmol) of sodiumt-butoxide were added thereto, and then heated under reflux at about120° C. for about 16 hours. After completion of the reaction, thereaction product was extracted with 100 ml of distilled water and 200 mlof ethyl acetate to obtain an organic layer, which was then dried usingmagnesium sulfate and distilled under reduced pressure. The resultingproduct was separated and purified using column chromatography to obtain2.6 g (3.4 mmol, Yield 52%) of Intermediate 39(1).

LC-MS m/z=778(M+H)+

Synthesis of Ligand 39 (L39)

After dissolving 2.0 g (2.7 mmol) of Intermediate 39(1) in 30 ml ofethanol at room temperature, 50 ml of a 4N diluted hydrochloric acidsolution was added thereto and heated under reflux at about 80° C. forabout 18 hours. After completion of the reaction, the reaction productwas concentrated under reduced pressure, and then extracted with 200 mlof dichloromethane to obtain an organic layer, which was then driedusing magnesium sulfate and distilled under reduced pressure. Theresulting product was separated and purified using column chromatographyto obtain 1.1 g (2.4 mmol, Yield 90%) of ligand 39 (L39).

LC-MS m/z=518(M+H)+

Ligand Synthesis 40: Synthesis of Ligand 40 (L40)

Ligand 40 (L40) was synthesized according to Reaction Scheme 40 below:

Synthesis of Intermediate 40(2)

After dissolving 5.0 g (47.6 mmol) of 2-cyanopyrimidine in 100 ml ofethanol at room temperature, 20 ml (475.7 mmol) of hydrazine hydrate wasadded thereto and stirred at room temperature for about two days. Aftercompletion of the reaction, the reaction product was concentrated underreduced pressure, and then extracted with 100 ml of salt water and 200ml of dichloromethane to obtain an organic layer, which was then driedusing magnesium sulfate and distilled under reduced pressure. Theresulting product was separated and purified using column chromatographyto obtain 3.0 g (21.9 mmol, Yield 46%) of Intermediate 40(2).

LC-MS m/z=138(M+H)+

Synthesis of Intermediate 40(1)

Following dissolving 40(2) 2.9 g (21.6 mmol) of Intermediate 40(2) in120 ml of anhydrous tetrahydrofuran and 40 ml of distilled water at roomtemperature, 2.7 g (32.1 mmol) of sodium hydrocarbonate was added to thereaction mixture at room temperature and stirred for about 30 minutes.After 30 minutes, 3.2 ml (25.9 mmol) of trimethyl ethylchloride wasslowly added thereto at 0° C. and stirred at room temperature for about16 hours. After completion of the reaction, the reaction product wasextracted with 100 ml of distilled water and 200 ml of dichloromethaneto obtain an organic layer, which was then dried using magnesium sulfateand distilled under reduced pressure. The resulting product wasseparated and purified using column chromatography to obtain 1.2 g (5.4mmol, Yield 25%) of Intermediate 40(1).

LC-MS m/z=222(M+H)+

Synthesis of Ligand 40 (L40)

After dissolving 1.2 g (5.4 mmol) of Intermediate 40(1) in 30 ml ofethylene glycol at room temperature, the resulting solution was heatedunder reflux at about 190° C. for about 4 hours. The resulting productwas dissolved in 30 ml of ethanol, and 50 ml of a 4N dilutedhydrochloric acid solution was added thereto and heated under reflux atabout 80° C. for about 18 hours. After completion of the reaction, thereaction product was extracted with 100 ml of distilled water and 200 mlof dichloromethane to obtain an organic layer, which was then driedusing magnesium sulfate and distilled under reduced pressure. Theresulting product was separated and purified using column chromatographyto obtain 0.7 g (3.4 mmol, Yield 64%) of ligand 40 (L40).

LC-MS m/z=204(M+H)+

Ligand Synthesis 41: Synthesis of Ligand 41 (L41)

Ligand 41 (L41) was synthesized in the same manner (Yield: 19%) as inthe synthesis of ligand 30 (L30) (Ligand Synthesis 30), except thatmethyl 6-methylpyrimidine-4-caboxylate, instead of methylpyrimidine-4-carboxylate, was used in synthesizing Intermediate 30(1).

LC-MS m/z=297(M+H)+

Ligand Synthesis 42: Synthesis of Ligand 42 (L42)

Ligand 42 (L42) was synthesized in the same manner (Yield: 9%) as in thesynthesis of ligand 39 (L39) (Ligand Synthesis 39), except that3,3-dimethylbutan-2-one, instead of 1,1,1-trifluoropropan-2-one, wasused in synthesizing Intermediate 39(4).

LC-MS m/z=494(M+H)+

Ligand Synthesis 43: Synthesis of Ligand 43 (L43)

Ligand 43 (L43) was synthesized in the same manner (Yield: 7%) as in thesynthesis of ligand 39 (L39) (Ligand Synthesis 39), except that3,3-dimethylbutan-2-one, instead of 1,1,1-trifluoropropan-2-one, wasused in synthesizing Intermediate 39(4), and p-a, instead of aniline,was used in synthesizing intermediate 39(1).

LC-MS m/z=508(M+H)+

Synthesis Example 1: Synthesis of Compound 1

Compound 1 was synthesized according to Reaction Scheme 41 below:

After dissolving 1.0 g (6.8 mmol) of ligand 1 (L1) in 50 ml of anaqueous ethanol solution at room temperature, 1.4 g (3.4 mmol) ofK2PtCl4 was added thereto and heated under reflux at about 100° C. forabout 18 hours. After 18 hours, the reaction product was cooled to 0° C.to obtain a solid product, which was then filtered. The filtrated solidwas rinsed with 80 ml of hot water and then with 50 ml of hot ethanol.The resulting product was separated and purified using columnchromatography, and further purified by sublimation to obtain 0.6 g (1.2mmol, Yield 19%) of Compound 1.

LC-MS m/z=486(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=10.72 (s, 1H), 8.84 (d, 1H), 7.72 (d, 1H),7.53 (d, 2H), 6.36 (d, 1H)

Synthesis Example 2: Synthesis of Compound 2

Compound 2 (Yield 22%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 4 (L4), instead of ligand 1(L1), was used.

LC-MS m/z=514(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=10.97 (s, 1H), 8.68 (d, 1H), 7.47 (d, 1H),6.58 (s, 1H), 2.92 (s, 3H)

Synthesis Example 3: Synthesis of Compound 3

Compound 3 (Yield 42%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 5 (L5), instead of ligand 1(L1), was used.

LC-MS m/z=570(M+H)+

1H NMR (300 MHz, CDCl3) σ=11.00 (s, 1H), 8.71 (d, 1H), 7.32 (d, 1H),6.72 (s, 1H), 3.72 (m, 1H), 1.28 (d, 6H)

Synthesis Example 4: Synthesis of Compound 4

Compound 4 (Yield 35%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 6 (L6), instead of ligand 1(L1), was used.

LC-MS m/z=598(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=11.10 (s, 1H), 8.73 (d, 1H), 7.56 (d, 1H),6.64 (s, 1H), 1.43 (s, 9H)

Synthesis Example 5: Synthesis of Compound 5

Compound 5 (Yield 32%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 7 (L7), instead of ligand 1(L1), was used.

LC-MS m/z=622(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=11.07 (s, 1H), 8.81 (d, 1H), 7.61 (d, 1H),6.14 (s, 1H)

Synthesis Example 6: Synthesis of Compound 6

Compound 6 (Yield 29%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 8 (L8), instead of ligand 1(L1), was used.

LC-MS m/z=594(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=10.96 (s, 1H), 9.17 (d, 1H), 8.17 (d, 1H),2.76 (br s, 2H), 2.72 (br s, 2H), 1.79˜1.73 (br s, 4H)

Synthesis Example 7: Synthesis of Compound 7

Compound 7 (Yield 28%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 9 (L9), instead of ligand 1(L1), was used.

LC-MS m/z=650(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=11.01 (s, 1H), 9.26 (d, 1H), 8.32 (d, 1H),2.71 (br s, 2H), 1.82 (br s, 2H), 1.54 (br s, 2H), 1.38 (s, 6H)

Synthesis Example 8: Synthesis of Compound 8

Compound 8 (Yield 17%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 10 (L10), instead of ligand 1(L1), was used.

LC-MS m/z=702(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=11.03 (s, 1H), 9.23 (d, 1H), 8.37 (d, 1H),2.77 (br s, 1H), 1.68˜1.62 (m, 4H), 1.47 (s, 3H), 1.01 (s, 6H)

Synthesis Example 9: Synthesis of Compound 9

Compound 9 (Yield 36%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 11 (L11), instead of ligand 1(L1), was used.

LC-MS m/z=542(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=10.36 (s, 1H), 8.48 (s, 1H), 6.21 (s, 1H),2.36 (s, 3H), 2.33 (s, 6H)

Synthesis Example 10: Synthesis of Compound 10

Compound 10 (Yield 48%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 12 (L12), instead of ligand 1(L1), was used.

LC-MS m/z=626(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=10.34 (s, 1H), 8.42 (s, 1H), 6.01 (s, 1H),2.32 (s, 3H), 1.36 (s, 9H)

Synthesis Example 11: Synthesis of Compound 11

Compound 11 (Yield 42%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 13 (L13), instead of ligand 1(L1), was used.

LC-MS m/z=650(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=10.41 (s, 1H), 8.19 (s, 1H), 6.02 (s, 1H),2.33 (s, 3H)

Synthesis Example 12: Synthesis of Compound 12

Compound 12 (Yield 49%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 14 (L14), instead of ligand 1(L1), was used.

LC-MS m/z=678(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=10.34 (s, 1H), 8.36 (s, 1H), 2.77 (br s, 2H),2.29 (s, 3H), 1.82 (br s, 2H), 1.55 (br s, 2H), 1.36 (s, 614)

Synthesis Example 13: Synthesis of Compound 13

Compound 13 (Yield 36%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 15 (L15), instead of ligand 1(L1), was used.

LC-MS m/z=730(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=10.31 (s, 1H), 8.28 (s, 1H), 2.82 (br s, 1H),2.31 (s, 1H), 1.66˜1.62 (m, 4H), 1.45 (s, 3H), 0.99 (s, 6H)

Synthesis Example 14: Synthesis of Compound 14

Compound 14 (Yield 28%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 16 (L16), instead of ligand 1(L1), was used.

LC-MS m/z=574(M+H)+

1H NMR (300 MHz, CDCl₃) σ=10.06 (s, 1H), 7.84 (s, 1H), 6.36 (s, 1H),3.65 (s, 3H), 2.21 (s, 3H)

Synthesis Example 15: Synthesis of Compound 15

Compound 15 (Yield 34%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 17 (L17), instead of ligand 1(L1), was used.

LC-MS m/z=658(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=10.00 (s, 1H), 7.69 (s, 1H), 6.12 (s, 1H),3.67 (s, 3H), 1.42 (s, 9H)

Synthesis Example 16: Synthesis of Compound 16

Compound 16 (Yield 27%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 18 (L18), instead of ligand 1(LI), was used.

LC-MS m/z=682(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=10.13 (s, 1H), 7.42 (s, 1H), 6.02 (s, 1H),3.80 (s, 3H)

Synthesis Example 17: Synthesis of Compound 17

Compound 17 (Yield 22%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 19 (L19), instead of ligand 1(L1), was used.

LC-MS m/z=694(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=10.03 (s, 1H), 7.76 (s, 1H), 3.83 (s, 3H),2.76 (s, 2H), 1.76 (br s, 2H), 1.54 (br s, 2H), 1.36 (s, 6H)

Synthesis Example 18: Synthesis of Compound 18

Compound 18 (Yield 19%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 20 (L20), instead of ligand 1(L1), was used.

LC-MS m/z=762(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=10.10 (s, 1H), 7.81 (s, 1H), 3.81 (s, 3H),2.72 (br s, 1H), 1.69˜1.65 (m, 4H), 1.43 (s, 3H), 0.99 (s, 6H)

Synthesis Example 19: Synthesis of Compound 19

Compound 19 (Yield 21%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 21 (L21), instead of ligand 1(L1), was used.

LC-MS m/z=650(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=11.07 (s, 1H), 8.51 (s, 1H), 6.41 (s, 1H),2.21 (s, 3H)

Synthesis Example 20: Synthesis of Compound 20

Compound 20 (Yield 38%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 22 (L22), instead of ligand 1(L1), was used.

LC-MS m/z=734(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=11.00 (s, 1H), 8.38 (s, 1H), 6.28 (s, 1H),1.58 (s, 9H)

Synthesis Example 21: Synthesis of Compound 21

Compound 21 (Yield 42%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 23 (L23), instead of ligand 1(L1), was used.

LC-MS m/z=758(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=11.02 (s, 1H), 8.13 (s, 1H), 6.53 (s, 1H)

Synthesis Example 22: Synthesis of Compound 22

Compound 22 (Yield 37%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 24 (L24), instead of ligand 1(L1), was used.

LC-MS m/z=838(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=11.12 (s, 1H), 8.31 (s, 1H), 2.96-2.94 (m,1H), 1.93-1.89 (m, 2H), 1.69˜1.65 (m, 2H), 1.42 (s, 3H), 0.99 (s, 6H)

Synthesis Example 23: Synthesis of Compound 23

Compound 23 (Yield 35%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 25 (L25), instead of ligand 1(L1), was used.

LC-MS m/z=626(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=8.87 (d, 1H), 7.68 (d, 1H), 6.32 (s, 1H), 2.63(s, 3H), 1.33 (s, 9H)

Synthesis Example 24: Synthesis of Compound 24

Compound 24 (Yield 21%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 26 (L26), instead of ligand 1(L1), was used.

LC-MS m/z=650(M+H)+

¹H NMR (300 MHz, CDCl₃) c=8.76 (d, 1H), 7.53 (d, 1H), 6.48 (s, 1H), 2.44(s, 3H)

Synthesis Example 25: Synthesis of Compound 25

Compound 27 (Yield 36%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 27 (L27), instead of ligand 1(L1), was used.

LC-MS m/z=626(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=11.32 (s, 1H), 9.21 (d, 1H), 8.17 (d, 1H),2.04 (s, 3H), 1.36 (s, 9H)

Synthesis Example 26: Synthesis of Compound 26

Compound 26 (Yield 34%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 28 (L28), instead of ligand 1(L1), was used.

LC-MS m/z=710(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=11.23 (s, 1H), 8.78 (d, 1H), 8.05 (d, 1H),1.41 (s, 9H), 1.33 (s, 9H)

Synthesis Example 27: Synthesis of Compound 27

Compound 27 (Yield 21%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 29 (L29), instead of ligand 1(L1), was used.

LC-MS m/z=734(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=11.18 (s, 1H), 9.13 (d, 1H), 8.15 (d, 1H),1.38 (s, 9H)

Synthesis Example 28: Synthesis of Compound 28

Compound 28 (Yield 35%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 30 (L30), instead of ligand 1(L1), was used.

LC-MS m/z=758(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=11.13 (s, 1H), 8.86 (d, 1H), 7.64 (d, 1H)

Synthesis Example 29: Synthesis of Compound 68

Compound 68 (Yield 27%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 40 (L40), instead of ligand 1(L1), was used.

LC-MS m/z=600(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=10.86 (s, 1H), 8.92 (d, 1H), 7.73 (d, 1H),1.35 (2, 9H)

Synthesis Example 30: Synthesis of Compound 37

Compound 37 (Yield 22%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 2 (L2), instead of ligand 1(L1), was used.

LC-MS m/z=586(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=10.47 (s, 1H), 9.20 (d, 1H), 8.32 (d, 1 h),8.17 (d, 1H), 7.92 (d, 1H), 7.62 (m, 1H), 7.48 (m, 1H)

Synthesis Example 31: Synthesis of Compound 38

Compound 38 (Yield 26%) was synthesized in the same manner as inSynthesis Example 1, except that ligand 3 (L3), instead of ligand 1(L1), was used.

LC-MS m/z=686(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=10.54 (s, 1H), 8.46 (m, 1H), 7.84 (m, 1H),7.58 (m, 1H), 7.34 (d, 1H), 6.31 (d, 1H)

Synthesis Example 32: Synthesis of Compound 29

Compound 29 was synthesized according to Reaction Scheme 42 below:

Following dissolving 0.1 g (4.9 mmol) of NaH in 50 ml of anhydroustetrahydrofuran at 0° C., 1.0 g (4.8 mmol) of ligand 31 (L31) was slowlyadded thereto. After 30 minutes, 1.1 g (2.4 mmol) of PtCl(SEt₂)₂ wasadded to the mixture, stirred at room temperature for about 1 hour, andthen heated under reflux at about 80° C. for about 18 hours. After 18hours the reaction product was extracted with 80 ml of distilled waterand 100 ml of dichloromethane to obtain an organic layer, which was thendried using magnesium sulfate and concentrated under reduced pressure.The resulting product was separated and purified using columnchromatography, followed by further purification by sublimation toobtain 0.4 g (0.6 mmol, Yield 28%) of Compound 29.

LC-MS m/z=614(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=10.32 (s, 1H), 8.36 (d, 1H), 7.83-7.81 (m,2H), 7.58 (br s, 1H), 7.43 (s, 1H), 2.04 (s, 3H)

Synthesis Example 33: Synthesis of Compound 30

Compound 30 (Yield 22%) was synthesized in the same manner as inSynthesis Example 32, except that ligand 32 (L32), instead of ligand 31(L31), was used.

¹H NMR (300 MHz, CDCl₃) σ=10.29 (s, 1H), 8.16 (d, 1H), 7.84-7.83 (m,2H), 7.55 (br s, 1H), 6.38 (s, 1H), 1.39 (s, 9H)

Synthesis Example 34: Synthesis of Compound 31

Compound 31 (Yield 18%) was synthesized in the same manner as inSynthesis Example 32, except that ligand 33 (L33), instead of ligand 31(L31), was used.

¹H NMR (300 MHz, CDCl₃) σ=10.41 (s, 1H), 8.31 (d, 1H), 7.85-7.81 (m,2H), 7.49 (br s, 1H), 6.02 (s, 1H)

Synthesis Example 35: Synthesis of Compound 32

Compound 32 (Yield 31%) was synthesized in the same manner as inSynthesis Example 32, except that ligand 34 (L34), instead of ligand 31(L31), was used.

¹H NMR (300 MHz, CDCl₃) σ=10.29 (s, 1H), 8.16 (d, 1H), 7.83-7.81 (m,2H), 7.52 (br s, 1H), 2.76-2.72 (m, 4H), 1.83-1.76 (m, 4H)

Synthesis Example 36: Synthesis of Compound 33

Compound 33 (Yield 27%) was synthesized in the same manner as inSynthesis Example 32, except that ligand 35 (L35), instead of ligand 31(L31), was used.

¹H NMR (300 MHz, CDCl₃) σ=10.36 (s, 1H), 8.21 (d, 1H), 7.86-7.84 (m,2H), 7.56 (br s, 1H), 2.74-2.72 (m, 2H), 1.82-1.79 (m, 2H), 1.58-1.54(m, 2H), 1.42 (s, 6H)

Synthesis Example 37: Synthesis of Compound 34

Compound 34 (Yield 25%) was synthesized in the same manner as inSynthesis Example 32, except that ligand 36 (L36), instead of ligand 31(L31), was used.

¹H NMR (300 MHz, CDCl₃) σ=10.28 (s, 1H), 8.18 (d, 1H), 7.84-7.83 (m,2H), 7.58 (br s, 1H), 2.77-2.75 (m, 2H), 1.93-1.90 (m, 2H), 1.87-1.85(m, 2H), 1.47 (s, 3H), 1.02 (s, 6H)

Synthesis Example 38: Synthesis of Compound 35

Compound 35 (Yield 22%) was synthesized in the same manner as inSynthesis Example 32, except that ligand 37 (L37), instead of ligand 31(L31), was used.

¹H NMR (300 MHz, CDCl₃) σ=10.29 (s, 1H), 8.16 (d, 1H), 7.86-7.84 (m,2H), 7.61 (br s, 1H), 2.12 (s, 3H), 1.37 (s, 9H)

Synthesis Example 39: Synthesis of Compound 36

Compound 36 (Yield 21%) was synthesized in the same manner as inSynthesis Example 32, except that ligand 38 (L38), instead of ligand 31(L31), was used.

¹H NMR (300 MHz, CDCl₃) σ=10.16 (s, 1H), 8.35 (d, 1H), 7.73-7.71 (m,2H), 7.55 (br s, 1H), 1.35 (s, 9H)

Synthesis Example 40: Synthesis of Compound 39

Compound 39 was synthesized according to Reaction Scheme 43 below:

Synthesis of Compound 39(1)

Following dissolving 1.0 g (4.7 mmol) of ligand 7 (L7) and 1.9 g (4.7mmol) of K₂PtCl₄ in 100 ml of distilled water at room temperature, 3 mlof a 4N diluted hydrochloric acid was added thereto and heated underreflux at about 80° C. for about 6 hours. After 6 hours the reactionproduct was cooled to room temperature and filtered to obtain a solidcompound, which was then rinsed with 50 ml of distilled water and driedto obtain 2.0 g (2.4 mmol, Yield: 50%) of Compound 39(1).

Synthesis of Compound 39

Following dissolving 0.1 g (4.9 mmol) of NaH in 50 ml of anhydroustetrahydrofuran at 0° C. 0.4 g (2.4 mmol) of ligand 4 (L4) was slowlyadded thereto. After about 30 minutes, 2.0 g (2.4 mmol) of Compound39(1) was added thereto and heated under reflux at about 80° C. forabout 18 hours. After 18 hours, the reaction product was extracted with80 ml of distilled water and 100 ml of dichloromethane to obtain anorganic layer, which was then dried using magnesium sulfate andconcentrated under reduced pressure. The resulting product was separatedand purified using column chromatography, followed by furtherpurification by sublimation to obtain 0.6 g (1.2 mmol, Yield 48%) ofCompound 39.

LC-MS m/z=568(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=11.32 (s, 1H), 11.26 (s, 1H), 8.92 (d, 1H),8.76 (d, 1H), 6.75 (s, 1H), 6.64 (s, 1H), 2.32 (s, 3H)

Synthesis Example 41: Synthesis of Compound 40

Compound 40 (Yield 9%) was synthesized in the same manner as inSynthesis Example 40, except that ligand 6 (L6) was used, instead ofligand 4 (L4) used in synthesizing Compound 39.

¹H NMR (300 MHz, CDCl₃) σ=11.29 (s, 1H), 11.19 (s, 1H), 8.96 (d, 1H),8.65 (d, 1H), 6.81 (s, 1H), 6.68 (s, 1H), 1.35 (s, 9H)

Synthesis Example 42: Synthesis of Compound 41

Compound 41 (Yield 12%) was synthesized in the same manner as inSynthesis Example 40, except that ligand 27 (L27) was used, instead ofligand 4 (L4) used in synthesizing Compound 39.

¹H NMR (300 MHz, CDCl₃) σ=11.30 (s, 1H), 11.24 (s, 1H), 8.90 (d, 1H),8.71 (d, 1H), 6.72 (s, 1H), 2.04 (s, 3H), 1.33 (s, 9H)

Synthesis Example 43: Synthesis of Compound 42

Compound 42 (Yield 10%) was synthesized in the same manner as inSynthesis Example 40, except that ligand 29 (L29) was used, instead ofligand 4 (L4) used in synthesizing Compound 39.

¹H NMR (300 MHz, CDCl₃) σ=11.29 (s, 1H), 11.21 (s, 1H), 8.91 (d, 1H),8.56 (d, 1H), 6.70 (s, 1H), 1.38 (s, 9H)

Synthesis Example 44: Synthesis of Compound 43

Compound 43 (Yield 11%) was synthesized in the same manner as inSynthesis Example 40, except that ligand 30 (L30) was used, instead ofligand 4 (L4) used in synthesizing Compound 39.

¹H NMR (300 MHz, CDCl₃) σ=11.32 (s, 1H), 11.15 (s, 1H), 8.92 (d, 1H),8.72 (d, 1H), 6.72 (s, 1H)

Synthesis Example 45: Synthesis of Compound 44

Compound 44 (Yield 12%) was synthesized in the same manner as inSynthesis Example 40, except that ligand 13 (L13), instead of ligand 7(L7) used in synthesizing Compound 39(1), and ligand 30 (L30), insteadof ligand 4 (L4) used in synthesizing Compound 39, were used.

¹H NMR (300 MHz, CDCl₃) σ=11.16 (s, 1H), 11.26 (s, 1H), 9.21 (d, 1H),8.64 (d, 1H), 6.68 (s, 1H), 2.36 (s, 3H)

Synthesis Example 46: Synthesis of Compound 45

Compound 45 (Yield 11%) was synthesized in the same manner as inSynthesis Example 40, except that ligand 13 (L13), instead of ligand 7(L7) used in synthesizing Compound 39(1), and ligand 41 (L41), insteadof ligand 4 (L4) used in synthesizing Compound 39, were used.

¹H NMR (300 MHz, CDCl₃) σ=11.13 (s, 1H), 11.10 (s, 1H), 8.07 (d, 1H),8.02 (d, 1H), 6.35 (s, 1H)

Synthesis Example 47: Synthesis of Compound 46

Compound 46 (Yield 7%) was synthesized in the same manner as inSynthesis Example 40, except that ligand 31 (L31) was used, instead ofligand 4 (L4) used in synthesizing Compound 39.

¹H NMR (300 MHz, CDCl₃) σ=11.33 (s, 1H), 11.26 (s, 1H), 10.85 (d, 1H),8.63 (d, 1H), 8.54 (br s, 1H), 7.85-7.83 (m, 2H), 7.58 (br s, 1H), 6.85(s, 1H), 6.33 (s, 1H), 2.33 (s, 3H)

Synthesis Example 48: Synthesis of Compound 47

Compound 47 (Yield 10%) was synthesized in the same manner as inSynthesis Example 40, except that ligand 42 (L42) was used, instead ofligand 4 (L4) used in synthesizing Compound 39.

¹H NMR (300 MHz, CDCl₃) σ=11.32 (s, 1H), 9.20 (d, 1H), 8.85 (d, 1H),8.57 (d, 1H), 8.05-8.03 (m, 1H), 7.87-7.85 (m, 1H), 6.39 (s, 1H), 6.32(s, 1H)

Synthesis Example 49: Synthesis of Compound 48

Compound 48 (Yield 12%) was synthesized in the same manner as inSynthesis Example 40, except that ligand 43 (L43) was used, instead ofligand 4 (L4) used in synthesizing Compound 39.

¹H NMR (300 MHz, CDCl₃) σ=11.23 (s, 1H), 9.52 (d, 1H), 8.55 (d, 1H),8.31 (d, 1H), 8.16-8.14 (m, 1H), 7.92-7.90 (m, 1H), 6.35 (s, 1H), 6.33(s, 1H), 1.37 (s, 911)

Synthesis Example 50: Synthesis of Compound 49

Compound 49 (Yield 11%) was synthesized in the same manner as inSynthesis Example 40, except that ligand 6 (L6), instead of ligand 7(L7) used in synthesizing Compound 39(1), and ligand 43 (L43), insteadof ligand 4 (L4) used in synthesizing Compound 39, were used.

¹H NMR (300 MHz, CDCl₃) σ=11.13 (s, 1H), 9.86 (d, 1H), 8.71 (d, 1H),8.46 (d, 1H), 8.09-8.07 (m, 1H), 7.88-7.87 (m, 1H), 6.39 (s, 1H), 6.30(s, 1H), 1.37 (s, 9H), 1.35 (s, 9H)

Synthesis Example 51: Synthesis of Compound 50

Compound 50 (Yield 16%) was synthesized in the same manner as inSynthesis Example 40, except that 2-phenylpyridine was used, instead ofligand 4 (L4) used in synthesizing Compound 39.

¹H NMR (300 MHz, CDCl₃) σ=11.21 (s, 1H), 9.20 (d, 1H), 8.56 (d, 1H),8.30 (d, 1H), 8.17 (d, 1H), 7.97 (d, 1H), 7.51-7.47 (m, 3H), 7.41 (br s,1H), 7.02-7.00 (m, 1H), 6.32 (s, 1H)

Synthesis Example 52: Synthesis of Compound 51

Compound 51 (Yield 14%) was synthesized in the same manner as inSynthesis Example 40, except that ligand 6 (L6), instead of ligand 7(L7) used in synthesizing Compound 39(1), and 2-phenylpyridine, insteadof ligand 4 (L4) used in synthesizing Compound 39, were used.

¹H NMR (300 MHz, CDCl₃) σ=11.18 (s, 1H), 9.17 (d, 1H), 8.48 (d, 1H),8.36 (d, 1H), 8.21 (d, 1H), 7.88 (d, 1H), 7.55-7.51 (m, 3H), 7.36 (br s,1H), 7.02-7.00 (m, 1H), 6.33 (s, 1H), 1.38 (s, 9H)

Synthesis Example 53: Synthesis of Compound 52

Compound 52 (Yield 16%) was synthesized in the same manner as inSynthesis Example 40, except that ligand 9 (L9), instead of ligand 7(L7) used in synthesizing Compound 39(1), and 2-phenylpyridine, insteadof ligand 4 (L4) used in synthesizing Compound 39, were used.

¹H NMR (300 MHz, CDCl₃) σ=11.22 (s, 1H), 9.20 (d, 1H), 8.53 (d, 1H),8.31 (d, 1H), 8.15 (d, 1H), 8.02 (d, 1H), 7.50-7.46 (m, 3H), 7.43 (br s,1H), 7.05-7.03 (m, 1H), 2.76-2.74 (m, 2H), 1.79-1.77 (m, 2H), 1.54-1.52(m, 2H), 1.38 (s, 6H)

Synthesis Example 54: Synthesis of Compound 53

Compound 53 (Yield 26%) was synthesized in the same manner as inSynthesis Example 40, except that ligand 6 (L6), instead of ligand 7(L7) used in synthesizing Compound 39(1), and sodium acetylacetate(Na(acac)), instead of ligand 4 (L4) used in synthesizing Compound 39,were used.

¹H NMR (300 MHz, CDCl₃) σ=10.89 (s, 1H), 9.20 (d, 1H), 8.17 (d, 1H),6.21 (s, 1H), 5.31 (br s, 1H), 3.52-3.50 (m, 1H), 1.38 (s, 9H), 1.18 (s,6H)

Synthesis Example 55: Synthesis of Compound 54

Compound 54 (Yield 22%) was synthesized in the same manner as inSynthesis Example 40, except that sodium acetylacetate (Na(acac)) wasused, instead of ligand 4 (L4) used in synthesizing Compound 39.

¹H NMR (300 MHz, CDCl₃) σ=10.74 (s, 1H), 9.26 (d, 1H), 8.13 (d, 1H),6.36 (s, 1H), 5.33 (br s, 1H), 3.53-3.51 (m, 1H), 1.18 (s, 6H)

Synthesis Example 56: Synthesis of Compound 55

Compound 55 (Yield 26%) was synthesized in the same manner as inSynthesis Example 40, except that ligand 9 (L9), instead of ligand 7(L7) used in synthesizing Compound 39(1), and sodium acetylacetate(Na(acac)), instead of ligand 4 (L4) used in synthesizing Compound 39,were used.

¹H NMR (300 MHz, CDCl₃) σ=11.02 (s, 1H), 8.72 (d, 1 h), 8.58 (d, 1H),5.31 (br s, 1H), 3.52-3.50 (m, 1H), 2.75-2.73 (m, 2H), 1.79-1.76 (m,2H), 1.54-1.52 (m, 2H), 1.40 (s, 6H), 1.20 (s, 6H)

Synthesis Example 57: Synthesis of Compound 56

Compound 56 (Yield 21%) was synthesized in the same manner as inSynthesis Example 40, except that ligand 27 (L27), instead of ligand 7(L7) used in synthesizing Compound 39(1), and sodium acetylacetate(Na(acac)), instead of ligand 4 (L4) used in synthesizing Compound 39,were used.

¹H NMR (300 MHz, CDCl₃) σ=10.91 (s, 1H), 8.25 (d, 1 h), 7.85 (d, 1H),5.31 (br s, 1H), 3.52-3.50 (m, 1H), 2.75-2.73 (m, 2H), 2.10 (s, 3H),1.35 (s, 9H), 1.18 (s, 611)

Synthesis Example 58: Synthesis of Compound 57

Compound 57 was synthesized according to Reaction Scheme 44 below:

Following dissolving 2.0 mmol of ligand 39 (L39) in 30 ml ofbenzonitrile, 0.7 g (2.0 mmol) of PtCl4 was added thereto and stirred atabout 240° C. for about 36 hours. After 36 hours, the reaction productwas cooled to room temperature and filtered to obtain a solid product,which was rinsed with 50 ml of ether and dried to obtain Compound 37(Yield: less than 3%).

LC-MS m/z=711(M+H)+

Synthesis Example 59: Synthesis of Compound 58

Compound 58 (Yield 3%) was synthesized in the same manner as inSynthesis Example 58, except that ligand 44 (L44), instead of ligand 39(L39), was used.

LC-MS m/z=701(M+H)+

Synthesis Example 60: Synthesis of Compound 59

Compound 59 (Yield 7%) was synthesized in the same manner as inSynthesis Example 58, except that ligand 45 (L45), instead of ligand 39(L39), was used.

LC-MS m/z=701(M+H)+

¹H NMR (300 MHz, CDCl₃) σ=7.48-7.45 (m, 2H), 7.25-7.23 (m, 2H),6.99-6.97 (m, 2H), 6.66-6.63 (m, 2H), 6.51-6.49 (m, 2H), 6.32 (s, 2H),2.31 (s, 3H), 1.35 (s, 18H)

Synthesis Example 61: Synthesis of Compound 60

Compound 60 was synthesized according to Reaction Scheme 45 below:

Following dissolving 6.0 mmol of ligand 7 (L7) in 40 ml of diethyleneglycol monoethyl ether, 0.9 g (1.0 mmol) of Os₃(CO)₁₂ was added theretoand stirred at about 180° C. for about 24 hours. After the temperaturewas cooled to about 140° C., 0.4 g (5.0 mmol) of trimethylamine N-oxidewas added thereto and stirred at about 180° C. for about 5 minutes.After 5 minutes, 5.0 mmol of dimethyl(phenyl)phosphine (PPhMe2) wasadded thereto and stirred for about 24 hours. After completion of thereaction, the reaction product was extracted with 80 ml of distilledwater and 200 ml of dichloromethane to obtain an organic layer, whichwas then dried using magnesium sulfate and distilled under reducedpressure. The resulting product was separated and purified using columnchromatography, followed by further purification by sublimation toobtain Compound 60 (Yield 65%).

¹H NMR (300 MHz, CDCl₃) σ=11.19 (s, 2H), 7.62 (d, 2H), 7.05 (d, 2H),6.92-6.87 (m, 8H), 6.41-6.38 (m, 4H), 0.81 (m, 6H), 0.60 (m, 6H)

Synthesis Example 62: Synthesis of Compound 61

Compound 61 (Yield 62%) was synthesized in the same manner as inSynthesis Example 61, except that ligand 6 (L6), instead of ligand 7(L7) was used, and diphenyl(methyl)phosphine (PPh2Me), instead ofPPhMe2, was used.

¹H NMR (300 MHz, CDCl₃) σ=11.20 (s, 2H), 7.73 (d, 2H), 7.12 (d, 2H),6.96-6.93 (m, 8H), 6.46-6.43 (m, 4H), 1.37 (m, 18H), 0.81 (m, 6H), 0.60(m, 6H)

Synthesis Example 63: Synthesis of Compound 62

Compound 62 (Yield 62%) was synthesized in the same manner as inSynthesis Example 61, except that ligand 6 (L6), instead of ligand 7(L7), was used.

¹H NMR (300 MHz, CDCl₃) σ=11.17 (s, 2H), 7.55 (d, 2H), 7.32 (d, 2H),7.23-7.11 (m, 4H), 7.00-6.97 (m, 4H), 6395-6.92 (m, 4H), 6.89-6.85 (m,4H), 6.69-6.64 (m, 4H), 1.26 (t, 6H)

Synthesis Example 64: Synthesis of Compound 63

Compound 63 (Yield 22%) was synthesized in the same manner as inSynthesis Example 61, except that 1,2-bis(diphenylphospino)ethanol,instead of dimethyl(phenyl)phosphine (PPhMe2), was used.

¹H NMR (300 MHz, CDCl₃) σ=9.06-9.03 (m, 2H), 7.90-7.87 (m, 4H),7.78-7.75 (m, 2H), 7.43-7.41 (m, 2H), 7.35-7.31 (m, 4H), 7.30-7.27 (m,2H), 7.17-7.15 (m, 2H), 7.09-7.08 (m, 2H), 6.80-6.77 (m, 4H), 6.62-6.60(m, 4H), 6.41-6.38 (m, 2H)

Synthesis Example 65: Synthesis of Compound 64

Compound 64 (Yield 21%) was synthesized in the same manner as inSynthesis Example 61, except that ligand 6 (L6), instead of ligand 7(L7), and 1,2-bis(diphenylphospino)ethanol, instead ofdiphenyl(methyl)phosphine (PPh2Me), were used.

¹H NMR (300 MHz, CDCl₃) u=9.03-9.01 (m, 2H), 7.84-7.2 (m, 4H), 7.75-7.73(m, 2H), 7.46-7.44 (m, 2H), 7.43-7.40 (m, 4H), 7.35-7.32 (m, 2H),7.21-7.19 (m, 2H), 7.12-7.10 (m, 2H), 6.76-6.73 (m, 4H), 6.63-6.60 (m,4H), 6.53-6.51 (m, 2H), 1.37-1.34 (m, 18H)

Synthesis Example 66: Synthesis of Compound 65

Compound 65 was synthesized according to Reaction Scheme 46 below:

Following dissolving 2.0 mmol of ligand 4 (L4) in 30 ml ofethyleneglycol, 0.4 g (0.3 mmol) of IrCl₃.3H₂O was added thereto andstirred at about 220° C. for about 24 hours. After completion of thereaction, the reaction product was extracted with 50 ml of distilledwater and 100 ml of methylenechloride to obtain an organic layer, whichwas then dried using magnesium sulfate and distilled under reducedpressure. The resulting product was separated and purified using columnchromatography to obtain Compound 65 (Yield 26%).

LC-MS m/z=671(M+H)+

Synthesis Example 67: Synthesis of Compound 66

Compound 66 (Yield 22%) was synthesized in the same manner as inSynthesis Example 66, except that ligand 7 (L7), instead of ligand 4(L4), was used.

LC-MS m/z=833(M+H)+

Synthesis Example 68: Synthesis of Compound 67

Compound 67 was synthesized according to Reaction Scheme 47 below:

1.5 g (7.1 mmol) of 2,6-dipyrazole-1-yl pyridine as a start material and2.6 g (2.0 mmol) of IrCl₃.3H₂O were dissolved in 60 ml of methanol andheated under reflux for about 15 hours. Afterward, the reaction productwas cooled and filtered to obtain a solid product, which was then driedand dissolved in 120 ml of glycerol. 4.5 g (21.3 mmol) of ligand 7 (L7)was added to the reaction mixture and subjected to microwave radiation(300 W) for about 3 hours for reaction. After completion of thereaction, 200 ml of a saturated salt solution was added to the reactionproduct and filtered to obtain a solid product, which was then dried andrecrystallized using a mixed solvent of dichloromethane and hexane. Theresulting solid compound was dissolved in 80 ml of glycerol, andsubjected to microwave radiation (300 W) for about 6 hours with anaddition of potassium hydroxide. After completion of the reaction, thereaction product was extracted with 100 ml of a saturated salt solutionand 300 ml of methylenechloride at room temperature to obtain an organiclayer, which was then dried using magnesium sulfate and distilled underreduced pressure. The resulting product was separated and purified usingcolumn chromatography to obtain Compound 67 (Yield 2%).

LC-MS m/z=719(M+H)+

Example 1

A glass substrate with an anode (ITO/Ag/ITO deposited to a thickness of70 Å/1000 Å/70 Å, respectively) was cut to a size of 50 mm×50 mm×0.5 mmand then sonicated in isopropyl alcohol and pure water each for fiveminutes, and then cleaned by irradiation of ultraviolet rays for 30minutes and exposure to ozone. The resulting glass substrate was loadedinto a vacuum deposition device.

2-TNATA was deposited on a surface of the anode to form an HIL having athickness of 600 Å, and then4.4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was deposited onthe HIL to form a HTL having a thickness of 1000 Å.

CBP (host) and Compound 2 (dopant) were co-deposited in a weight ratioof 95:5 on a surface of the HTL to form an EML having a thickness ofabout 400 Å, followed by deposition of BCP on the EML to form a HBLhaving a thickness of about 50 Å. Then, Alq₃ was deposited on the HBL toform an ETL having a thickness of about 350 Å, and then LiF wasdeposited on the ETL to form an EIL having a thickness of about 10 Å.Then, Mg and Ag were deposited in a weight ratio of 90:10 on the EIL toform a cathode having a thickness of about 120 Å, thereby completing themanufacture of an organic light-emitting device.

Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 3, instead of Compound 2, was used toform the EML.

Example 3

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 4, instead of Compound 2, was used toform the EML.

Example 4

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 6, instead of Compound 2, was used toform the EML.

Example 5

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 7, instead of Compound 2, was used toform the EML.

Example 6

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 68, instead of Compound 2, was usedto form the EML.

Example 7

An organic light-emitting device was manufactured in the same manner asin Example 1, except that the thickness of the HTL was changed to about1350 Å, and CBP (host) and Compound 30 (dopant) were co-deposited in aweight ratio of 94:6 to form an EML having a thickness of about 400 Å.

Example 8

An organic light-emitting device was manufactured in the same manner asin Example 7, except that Compound 33, instead of Compound 30, was usedto form the EML.

Example 9

An organic light-emitting device was manufactured in the same manner asin Example 7, except that Compound 34, instead of Compound 30, was usedto form the EML.

Example 10

An organic light-emitting device was manufactured in the same manner asin Example 7, except that Compound 60, instead of Compound 30, was usedto form the EML.

Example 11

An organic light-emitting device was manufactured in the same manner asin Example 7, except that Compound 63, instead of Compound 30, was usedto form the EML.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Ir(ppy)₃, instead of Compound 2, was used toform the EML.

Comparative Example 2

An organic light-emitting device was manufactured in the same manner asin Example 7, except that PtOEP, instead of Compound 30, was used toform the EML.

Comparative Example 3

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound A below, instead of Compound 2, wasused to form the EML.

Comparative Example 4

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound B below, instead of Compound 2, wasused to form the EML.

Evaluation Example 1

Driving voltages, current densities, luminescences, efficiencies, andcolor purities of the organic light-emitting devices of Examples 1 to 11and Comparative Examples 1 to 4 were measured using a PR650(Spectroscan) Source Measurement Unit. (available from Photo Research,Inc.). LT₉₇ is lifetime data as the time it takes for an initialluminescence (assumed as 100% at a current density of about 10 mA/cm² isreduced to 97%. The results are shown in Table 1 below, in which V_(dr)is driving voltage, Cmp is compound, L is luminance, Eff is efficiency,Clr is emission color, and Clr_(coor) is color coordinate.

TABLE 1 Current V_(dr) density L Eff LT₉₇ Host Dopant (V) (mA/cm²)(cd/m²) (cd/A) Clr Clr_(coor) (HR) Example 1 CBP Cmp 2 5.5 10 6,330 63.3green 0.29, 97 0.70 Example 2 CBP Cmp 3 5.6 10 6,521 65.2 green 0.26, 940.72 Example 3 CBP Cmp 4 5.5 10 6,870 68.7 green 0.27, 98 0.72 Example 4CBP Cmp 6 5.6 10 6,625 66.2 green 0.25, 92 0.71 Example 5 CBP Cmp 7 5.710 6,590 65.9 green 0.26, 93 0.71 Example 6 CBP Cmp 68 5.6 10 6,228 62.2green 0.28, 90 0.70 Example 7 CBP Cmp 30 5.9 10 3,042 30.4 red 0.65, 1210.34 Example 8 CBP Cmp 33 5.3 10 3,283 32.8 red 0.66, 116 0.37 Example 9CBP Cmp 34 5.3 10 3,330 33.3 red 0.66, 110 0.35 Example 10 CBP Cmp 605.5 10 3,570 35.7 red 0.64, 92 0.33 Example 11 CBP Cmp 63 5.6 10 3,48734.8 red 0.63, 105 0.34 Comp. CBP Ir(ppy)₃ 6.8 10 4,766 47.7 green 0.25,61 Example 1 0.70 Comp. CBP PtOEP 7.3 10 2,212 22.1 red 0.67, 89 Example2 0.32 Comp. CBP Cmp A 5.9 10 4,856 48.5 green 0.25, 76 Example 3 0.68Comp. CBP Cmp B 6.3 10 5,510 55.1 green 0.27, 55 Example 4 0.70

Referring to Table 1 above, the organic light-emitting device ofExamples 1 to 6 are found to be improved in terms of driving voltage,luminance, efficiency, and lifetime characteristics, relative to theorganic light-emitting devices of Comparative Examples 1, 3, and 4. Theorganic light-emitting device of Examples 7 to 11 are found haveimproved driving voltages, luminances, efficiencies, and lifetimecharacteristics, as compared with the organic light-emitting device ofComparative Example 2.

By way of summary and review, an OLED may have a structure including asubstrate, and an anode, a hole transport layer (HTL), an emission layer(EML), an electron transport layer (ETL), and a cathode which aresequentially stacked on the substrate. In this regard, the HTL, the EML,and the ETL may be organic thin films formed of organic compounds.

An operating principle of an OLED having the above-described structuremay be as follows. When a voltage is applied between the anode and thecathode, holes injected from the anode move to the EML via the HTL, andelectrons injected from the cathode move to the EML via the ETL. Theholes and electrons recombine in the EML to generate excitons. When theexcitons drop from an excited state to a ground state, light is emitted.

As described above, an organic light-emitting device including theorganometallic compounds according to one or more of the aboveembodiments may provide an OLED with a low driving voltage, a highefficiency, and a long lifetime.

Example embodiments have been disclosed herein, and although specificterms are employed, they are used and are to be interpreted in a genericand descriptive sense only and not for purpose of limitation. In someinstances, as would be apparent to one of ordinary skill in the art asof the filing of the present application, features, characteristics,and/or elements described in connection with a particular embodiment maybe used singly or in combination with features, characteristics, and/orelements described in connection with other embodiments unless otherwisespecifically indicated. Accordingly, it will be understood by those ofskill in the art that various changes in form and details may be madewithout departing from the spirit and scope of the present invention asset forth in the following claims.

What is claimed is:
 1. An organometallic compound represented by oneselected from the group of Formulae 5 to 8:

wherein, in Formulae 5 to 8: M is a transition metal; X₁ is N or C(R₅);R₁ to R₅ are each independently selected from the group of a hydrogenatom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, a phosphoric acid group or a salt thereof, a substitutedor unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstitutedC₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynylgroup, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substitutedor unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₃-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅),—C(═O)(Q₆), and a binding site with an adjacent ligand via a single bondor a divalent linking group, provided that when X₂₁ in Formula 5 isC(R₅₁), R₁ in Formula 5 is not a binding site with R₅₁ of an adjacentligand and provided that when X₂₇ in Formula 6 is C(R₅₇), R₁ in Formula6 is not a binding site with R₅₇ of an adjacent ligand; two substituentsof R₁ to R₅ are optionally linked together to form one selected from thegroup of a substituted or unsubstituted C₄-C₂₀ alicyclic ring, asubstituted or unsubstituted C₂-C₂₀ hetero alicyclic ring, a substitutedor unsubstituted C₆-C₂₀ aromatic ring, and a substituted orunsubstituted C₂-C₂₀ heteroaromatic ring; Q₁ to Q₆ are eachindependently selected from the group of a hydrogen atom, a substitutedor unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstitutedC₆-C₆₀ aryl group, and a substituted or unsubstituted C₂-C₆₀ heteroarylgroup; m2 is 0, 1, or 2, wherein when m2 is 1 or 2, L is a monodentate,bidentate, tridentate, or tetradentate organic ligand; X₁₂ and X_(16d)are each independently N or C; X₂₁ is N or C(R₅₁), X₂₂ is N or C(R₅₂),X₂₃ is N or C(R₅₃), X₂₄ is N or C(R₅₄), X₂₅ is N or C(R₅₅), X₂₆ is N orC(R₅₆), X₂₇ is N or C(R₅₇), X₂₈ is N or C(R₅₈), and X₂₉ is N or C(R₅₉);R₄₁, R₄₂, and R₅₁ to R₅₉ are each independently selected from the groupof a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₃-C₁₀ heterocycloalkyl group, a substituted orunsubstituted C₃-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₂-C₆₀ heteroaryl group, —N(Q₁₁)(Q₁₂),—Si(Q₁₃)(Q₁₄)(Q₁₅), and a binding site with an adjacent ligand via asingle bond or a divalent linking group; two adjacent substituents ofR₄₁, R₄₂, and R₅₁ to R₅₉ are optionally linked together to form oneselected from the group of a substituted or unsubstituted C₄-C₂₀alicyclic ring, a substituted or unsubstituted C₂-C₂₀ heteroalicyclicring, a substituted or unsubstituted C₆-C₂₀ aromatic ring, and asubstituted or unsubstituted C₂-C₂₀ heteroaromatic ring; and Q₁₁ to Q₁₅are each independently selected from the group of a hydrogen atom, aC₁-C₁₀ alkyl group, a C₆-C₂₀ aryl group, and a C₂-C₂₀ heteroaryl group.2. The organometallic compound as claimed in claim 1, wherein: theorganometallic compound is the organometallic compound represented byFormula 5 and the organometallic compound represented by Formula 5 isone selected from the group of Formulae 5-(1), 5-(2), 5-(3), and 5-(4):

wherein, in Formulae 5-(1) to 5-(4): M, X₁, X₂₁ to X₂₆, and R₁ to R₅ aredefined in Formulae 5 to 8; m2 is 0, 1, or 2, wherein when m2 is 1 or 2,L is as defined in Formulae 5 to 8; X₂₁ is N or C(R₅₁), X₂₂ is N orC(R₅₂), X₂₃ is N or C(R₅₃), X₂₄ is N or C(R₅₄), X₂₅ is N or C(R₅₅), andX₂₆ is N or C(R₅₆); and R₄₁, R₅₁ to R₅₆, R₆₁ to R₆₈, and R₇₁ to R₇₄ areeach independently selected from the group of a hydrogen atom, adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine, a hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a substituted C₁-C₂₀ alkyl group, asubstituted C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, ananthryl group, a fluorenyl group, a carbazolyl group, a pyridinyl group,a pyrimidinyl group, a triazinyl group, and a substituted cyclic groupthat is substituted with at least one selected from the group of: adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, and atriazinyl group; the substituted C₁-C₂₀ alkyl group and the substitutedC₁-C₂₀ alkoxy group are each substituted with at least one selected fromthe group of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, and an amino group; and the substituted cyclicgroup is selected from the group of a substituted phenyl group, asubstituted naphthyl group, a substituted anthryl group, a substitutedfluorenyl group, a substituted carbazolyl group, a substituted pyridinylgroup, a substituted pyrimidinyl group, and a substituted triazinylgroup.
 3. An organometallic compound represented by one selected fromthe group of Formulae 5-(a), 6-(a), and 7-(a):

wherein, in Formulae 5-(a), 6-(a), and 7-(a): M is a transition metal;X₁ is N or C(R₅); R₁ to R₅ are each independently selected from thegroup of a hydrogen atom, a deuterium atom, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₃-C₁₀ heterocycloalkyl group, a substituted orunsubstituted C₃-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₂-C₆₀ heteroaryl group, —N(Q₁)(Q₂),—Si(Q₃)(Q₄)(Q₅), —C(═O)(Q₆), and a binding site with an adjacent ligandvia a single bond or a divalent linking group; two substituents of R₁ toR₅ are optionally linked together to form one selected from the group ofa substituted or unsubstituted C₄-C₂₀ alicyclic ring, a substituted orunsubstituted C₂-C₂₀ hetero alicyclic ring, a substituted orunsubstituted C₆-C₂₀ aromatic ring, and a substituted or unsubstitutedC₂-C₂₀ heteroaromatic ring; Q₁ to Q₆ are each independently selectedfrom the group of a hydrogen atom, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, and asubstituted or unsubstituted C₂-C₆₀ heteroaryl group; B in Formula 6-(a)and 7-(a), m2 is 0, 1, or 2, and in Formula 5-(a), m2 is 1 or 2,wherein, when m2 is 1 or 2, L is a monodentate, bidentate, tridentate,or tetradentate organic ligand; X₁₂ is C or N; X₂₁ is N or C(R₅₁), X₂₂is N or C(R₅₂), X₂₃ is N or C(R₅₃), X₂₄ is N or C(R₅₄), X₂₅ is N orC(R₅₅), X₂₆ is N or C(R₅₆), and X₂₇ is N or C(R₅₇); R₄₁ and R₅₁ to R₅₇are each independently selected from the group of a hydrogen atom, adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine, a hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkyl group substituted with at least one fluorine atom,a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, and an anthrylgroup; Y₂ is a single bond or a divalent linking group including atleast one selected from the group of —O—, —S—, —N(Z₁₁)—,—[C(Z₁₂)(Z₁₃)]_(c)—, and —[Si(Z₁₄)(Z₁₅)]_(d)—; Z₁₁ to Z₁₅ are eachindependently selected from the group of a hydrogen atom, a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, C₁-C₆₀ alkyl group, a C₁-C₆₀alkyl group substituted with at least one halogen atom, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₃-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, or aC₂-C₆₀ heteroaryl group; and c and d are each independently an integerfrom 1 to
 4. 4. An organic light-emitting device, comprising: asubstrate; a first electrode; a second electrode opposite the firstelectrode; and an organic layer between the first electrode and thesecond electrode, the organic layer including the organometalliccompound as claimed in claim
 1. 5. An organic light-emitting device,comprising: a substrate; a first electrode; a second electrode oppositethe first electrode; and an organic layer between the first electrodeand the second electrode, the organic layer including the organometalliccompound as claimed in claim 3.